Heterocyclic Building Blocks-Tetrahydrofuran

124391-75-9, (S)-(Tetrahydrofuran-3-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

0267-1 Triethylamine (800 muL) was added to a solution of (tetrahydrofuran-3-yl)methanol (410 mg) in dichloromethane (4 mL), and methanesulfonyl chloride (350 muL) was added dropwise thereto under ice-cooling, followed by stirring at 0 C. for 30 minutes. Methanesulfonyl chloride (50 muL) was added thereto, followed by stirring at 0 C. for 30 minutes. The reaction mixture was purified by silica gel column chromatography (hexane-ethyl acetate), thereby obtaining (tetrahydrofuran-3-yl)methyl methanesulfonate (540 mg). 1H-NMR (CDCl3) delta: 4.21-4.10 (2H, m), 3.88-3.63 (4H, m), 3.05 (3H, s), 2.75-2.64 (1H, m), 2.18-2.04 (1H, m), 1.76-1.62 (1H, m).

As the paragraph descriping shows that 124391-75-9 is playing an increasingly important role.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

219823-47-9, (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of tri-tert-butyl hydrazine-1,1,2-tricarboxylate (58.5 g, 0.95 eq., prepared as per Angew. Chem. Tnt. Ed. 1996, 35, No. 22, 2626-2627) in dimethylsulfoxide (180 ml), was added cesium carbonate (90.77 g, 1.5 eq.), followed by stirring for 30 minutes at 20 to 30C. (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate (45.0 g, 1.0 eq.) was added into the reaction mass, followed by increase of temperature to 50 to 55C. The resulting reaction mass was stirred at 50 to 55C till tri-tert-butyl hydrazine-1,1,2-tricarboxylate is less than 0.25% monitored by HPLC area %. After completion of the reaction, the reaction mass was cooled to 20 to 25C, followed by addition of water (225 ml) and methyl tert-butyl ether (450 ml). The resulting biphasic mixture was stirred for 10 minutes followed by layer separation. The resulting organic layer was washed with an aqueous sodium chloride solution (225m1) followed by solvent evaporation under reduced pressure to give crude (5)-tri-tert-butyl 2-(tetrahydrofuran-3-yl)hydrazine- 1,1 ,2-tricarboxylate (68.34 g). The crude material was recrystallized using a mixture of methyl tert-butyl ether and n-heptane (22.5 ml:112.50 ml) to give pure (5)-tri-tert-butyl2-(tetrahydrofuran-3-yl)hydrazine- 1,1 ,2-tricarboxylate (57.96 g , 77.53%).Mass [M+Hj: 402.80Purity by HPLC: 99.59% areaSpecific Optical Rotation (C=1, Methanol): -8.553Melting point (DSC method): 62.7 1C

As the paragraph descriping shows that 219823-47-9 is playing an increasingly important role.

Reference£º
Patent; EISAI R&D MANAGEMENT CO., LTD.; KHILE, Anil Shahaji; NAYAK, Ranjeeta; DIXIT, Girish; (30 pag.)WO2016/21192; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.91470-28-9,Tetrahydrofuran-2-carboxamide,as a common compound, the synthetic route is as follows.

Preparation c-129 Tetrahydro-furan-2-carbonitrile Trifluoroacetic anhydride (1.55 g, 7.38 mmol) was added slowly, with a rate of one drop every 10 seconds, to an ice-cold solution (0 C.) of tetrahydro-furan-2-carboxylic acid amide (0.77 g, 6.71 mmol) and pyridine (1.06 g, 13.42 mmol) in anhydrous 1,4-dioxane (10 mL). The addition of trifluoroacetic anhydride was monitored to keep the internal temperature below 5 C. and was completed after 20 minutes. The resulting mixture was allowed to warm to ambient temperature, and stirred for 3 hours. Chloroform (100 mL) was added to the mixture, and then extracted with water (30 mL) and saturated aqueous sodium chloride (20 mL). The organic extracts were dried (anhydrous magnesium sulfate), filtered, and concentrated in vacuo to give the crude product. The residue was purified by flash column chromatography (hexanes to 25% ethyl acetate/hexanes) to afford the title compound (0.51 g, 62%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 4.70 (1H, m), 3.96 (2H, m), 2.24 (2H, m), 2.08 (2H, m).

91470-28-9 Tetrahydrofuran-2-carboxamide 3544692, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; Pfizer Inc; US2005/187266; (2005); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.118399-28-3,(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

A solution of (R)-benzyl-5-oxotetrahydrofuran-3-ylcarbamate (INTERMEDIATE 3, 18.4 g, 7.8 mmol) in THF (100 ml) was purged, at room temperature, with gaseous dimethylamine for 5 minutes. After stirring at room temp for 14 hours, the reaction mixture was concentrated to dryness, and purified by column chromatography (silica gel, eluting first with 50% ethyl acetate/hexanes followed by 100% acetone) to give the title product (20 g, yield: 91.5%).

118399-28-3 (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate 697924, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; ASTRAZENECA AB; US2012/35134; (2012); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.21461-84-7,(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic Acid,as a common compound, the synthetic route is as follows.

To a solution of 34 (1.09 g, 2.98 mmol) in dry THF (6 mL) was added a 1.5 M MeOH solution of hydrazine (6 mL). The resulting mixture was stirred at 55 C for 4 h and then poured into water and extracted with Et2O. The organic layer was washed with brine, dried (MgSO4), and concentrated to give a crude amine as a pale yellow oil. To another solution of 23 (412 mg, 3.17 mmol) and one drop of DMF in CH2Cl2 (8 mL) cooled in an ice-water bath was added slowly oxalyl chloride (0.32 mL, 3.73 mmol). The resulting mixture was stirred at rt for 2 h and then directly concentrated to give a liquid residue. This liquid was dissolved in THF (5 mL), cooled in a dry ice-acetone bath followed by the addition of Et3N (0.60 mL, 4.3 mmol) and a solution of the crude amine prepared above in THF (1 mL). The resulting mixture was stirred at rt overnight and then poured into water and extracted with CH2Cl2. The organic layer was dried (MgSO4), concentrated, and chromatographed on silica gel (hexane/EtOAc, 3:7) to give 675 mg (65%) of 36 as a yellow solid.

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Reference£º
Article; Chen, Ming-Jen; Tsai, Yeun-Min; Tetrahedron; vol. 67; 8; (2011); p. 1564 – 1574;,
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124391-75-9, (S)-(Tetrahydrofuran-3-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 51 (0.5g, 1.8mmol), 48 (0.381g, 2.7mmol) and triphenylphosphine (0.707g, 2.7mmol) in anhydrous THF (20mL) at 0¡ãC was added diisopropyl azodicarboxylate (DIAD) (0.545g, 2.7mmol) dropwise. The reaction mixture was allowed to stir at room temperature for 10min and then stirred at 40¡ãC overnight. The resulting mixture was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in 74 petroleum ether 2?5percent) to give the 172 product 52a as a white solid (0.365g, yield=50percent).

As the paragraph descriping shows that 124391-75-9 is playing an increasingly important role.

Reference£º
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

111769-27-8, (R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Procedure S3: To a solution of 3-[(4-fluoro-3-methyl-phenyl)carbamoyl]benzene- sulfonyl chloride (0.50 g, 1.52 mmol, 1 eq) and DIPEA (657 mu, 3.81 mmol, 2.5 eq) in CH2CI2 (10 mL), an amine (1.1 eq) was added. The reaction mixture was stirred for 1 hour. Next, 1M HC1 (5 mL) was added to the reaction mixture. Workup W2: The organic layer was separated and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography using a heptane to EtOAc gradient as eluent. Compound 129 Synthesis following procedure S3 with R-(+)-3-aminotetrahydrofuran toluene-4- sulfonate as amine, workup W2. Method F; Rt: 0.89 min. m/z: 396.1 (M+NH4)+ Exact mass: 378.1. 1 H NMR (400 MHz, DMSO-dg ) ppm 1.56 – 1.65 (m, 1 H), 1.85 – 1.94 (m, 1 H), 2.25 (d, J=1.8 Hz, 3 H), 3.36 (dd, J=9.0, 4.4 Hz, 1 H), 3.52 – 3.65 (m, 2 H), 3.65 – 3.73 (m, 1 H), 3.73 – 3.79 (m, 1 H), 7.14 (t, J=9.2 Hz, 1 H), 7.56 – 7.62 (m, 1 H), 7.67 (dd, J=7.0, 2.3 Hz, 1 H), 7.78 (t, J=7.8 Hz, 1 H), 7.99 – 8.05 (m, 1 H), 8.08 (bs, 1 H), 8.20-8.23(m, 1 H), 8.37 (t, J=1.7 Hz, 1 H), 10.47 (s, 1 H), []D = + 5.8 (c 0.61 w/v %, MeOH)

As the paragraph descriping shows that 111769-27-8 is playing an increasingly important role.

Reference£º
Patent; JANSSEN R&D IRELAND; LAST, Stefaan Julien; RABOISSON, Pierre Jean-Marie Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; WO2014/33170; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

88675-24-5, Tetrahydrofuran-3-amine is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (4S)-7-(6-methylpyridin-3-yl)-2,3,4,5-tetrahydro-l,4-methanopyrido[2,3- b][l,4]diazepine (300 mg, 1.189 mmol) in tetrahydrofuran (THF) (10 mL) triphosgene (176 mg, 0.594 mmol) was added at 0 C. After 30 min DIPEA (1.038 mL, 5.94 mmol), tetrahydrofuran-3 -amine (155 mg, 1.783 mmol) was added and the reaction mixture was stirred at 70 C for 16 h. The reaction was allowed to reach RT and then poured on cold water (50 mL) and extracted with ethyl acetate (2x 30 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to yield the crude product. The crude product was purified by flash column chromatography (silica-gel: 100- 200 mesh, eluent: 3% MeOH in DCM) to obtained (45)-7-(6-methylpyridin-3-yl)-N- (tetrahydrofuran-3 -yl)-3 ,4-dihydro- 1 ,4-methano pyrido[2,3 -b] [ 1 ,4]diazepine-5(2H)- carboxamide (137.1 mg, 0.371 mmol, 31.2 % yield) as an off white solid. (TLC system: Rf: 0.2, 5%MeOH-DCM), LCMS (m/z): 366.2 [M+H]+.1H NMR (400 MHz, CDC13): delta ppm 10.76 (br t, J=6.80 Hz, 1 H), 8.89 (s, 1 H), 7.99 (dd, J=8.22, 2.08 Hz, 1 H), 7.54 (d, J=7.89 Hz, 1 H), 7.30 – 7.21 (m, 2 H), 5.62 (dd, J=5.81, 2.96 Hz, 1 H), 4.56 (br dd, J=4.82, 1.97 Hz, 1 H), 4.01 – 3.75 (m, 4 H), 3.30 – 3.06 (m, 3 H), 2.99 – 2.91 (m, 1 H), 2.62 (s, 3 H), 2.39 – 2.21 (m, 2 H), 2.07 – 1.85 (m, 2 H).

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ELLIS, James Lamond; EVANS, Karen Anderson; FOX, Ryan Michael; MILLER, William Henry; SEEFELD, Mark Andrew; (766 pag.)WO2016/79709; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.

To a solution of 3/?-hydroxy-21 -oxolup-18-en-28-oic acid N-benzylamide (110 mg, 0.196 mmol) in 3 mL of pyridine is added 2,2-dimethyl succinic anhydride (75.3 mg, 0.588 mmol) and DMAP (28.6 mg, 0.235 mmol). The reaction mixture is stirred overnight under reflux. Then 75.3 mg of 2,2-dimethyl succinic anhydride is added twice every 3 hours to complete the reaction. The solvent is evaporated in vacuo and the residue is taken up with ethyl acetate (50 mL) and HCl 1 N (10 mL). The organic layer is washed with water (2 x 30 mL), brine (30 mL) and dried over sodium sulfate. The crude material is purified by flash chromatography (Biotage) on silica gel (ethyl acetate / hexanes 0 to 50percent) to give the title compound 9-1 (118.6 mg, 88percent) as a colorless solid.1 H NMR (400 MHz, CDCl3): delta [ppm] 7.34 – 7.21 (m, 5H), 5.61 (d x d, 1 H), 4.59 (d x d, 1 H), 4.50 (d x d, 1 H), 4.20 (d x d, 1 H), 3.19 (sept., 1 H), 2.67 (d, 1 H), 2.65 – 2.54 (m, 2H), 2.56 (d, 1H), 2.45 (d, 1 H), 2.17 (1 H), 1.85 – 0.74 (m, 18H), 1.3 (s, 3H), 1.29 (s, 3H), 1.2 (d, 3H), 1.18 (d, 3H), 0.89 (br s, 6H), 0.86 (s, 3H), 0.82 (s, 3H), 0.8 (s, 3H). LC/MS: m/z = 688.68 (M+H+).

The synthetic route of 17347-61-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VIROCHEM PHARMA INC.; CHAURET, Nathalie; WO2009/82818; (2009); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.

General procedure: Compound 6 (16 mg, 0.032 mmol), 2,2-dimethylsuccinic anhydride (41 mg, 0.32 mmol), DMAP (8 mg, 0.064 mmol) and pyridine (1.5 mL) were put into a 10 mL glass tube and sealed. The mixture was stirred at 120 C for about 12 h. The reaction mixture was then transferred into a 50 mL flask. Pyridine was removed under reduced pressure. 3N HCl (10 mL) was added, the mixture was extracted three times with EtOAc, and the organic layer washed with 3 N HCl for a second time. Then the organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc as eluent) to provide target product 8 (11 mg). White solid, yield 54%.

17347-61-4 2,2-Dimethylsuccinicanhydride 87067, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Article; Li, Jizhen; Goto, Masuo; Yang, Xiaoming; Morris-Natschke, Susan L.; Huang, Li; Chen, Chin-Ho; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 68 – 71;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem