Heterocyclic Building Blocks-Tetrahydrofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

5- (1-phenylcyclopropyl) isoxazole-3-carboxylic acid chloride ( In toluene solution (20 mL) Tetrahydrofuran-3-ylmethylamine hydrochloride (250 mg, 1.82 mmol) And 1 mol / L sodium hydroxide aqueous solution (20 mL) Were simultaneously added under cooling with ice water. After vigorously stirring for 30 minutes under cooling with ice water, The reaction mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, Represented by the following equation N- (tetrahydrofuran-3-ylmethyl) -5- (1-phenyl-cyclopropyl) isoxazole-3-carboxamide (Hereinafter referred to as the present amide compound (156)) 504 mg was obtained., 184950-35-4

As the paragraph descriping shows that 184950-35-4 is playing an increasingly important role.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Production Example 269 (0590) 5-(2,4-Difluorobenzyloxymethyl)isoxazole-3-carboxylic acid (1.20 g, 4.5 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.92 g, 6.7 mmol), triethylamine (0.93 mL, 6.7 mmol) and 1-hydroxybenzotriazole (0.06 g, 0.4 mmol) were added to chloroform (amylene addition product) (10 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.03 g, 5.4 mmol) was added to the mixture at room temperature, and the mixture was stirred overnight and then concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated saline water and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.78 g of N-(tetrahydrofuran-3-ylmethyl)-5-(2,4-difluorobenzyloxymeth yl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (278)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 1.63-1.72 (1H, m), 2.04-2.14 (1H, m), 2.52-2.63 (1H, m), 3.47 (2H, t), 3.59 (1H, dd), 3.73-3.80 (1H, m), 3.83-3.95(2H, m), 4.62(2H, s), 4.68 (2H, s), 6.74(1H, s), 6.81(1H, dt), 6.89(1H, dt), 6.93(1H, br s), 7.35-7.42(1H, m), 184950-35-4

As the paragraph descriping shows that 184950-35-4 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); 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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Production Example 128 (0444) 5-(3-Phenylpropoxymethyl)isoxazole-3-carboxylic acid (0.60 g, 2.3 mmol) was added to chloroform (amylene addition product) (12 mL), and cooled to 0C. Triethylamine (0.48 ml, 3.4 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.66 g, 3.4 mmol) and 1-hydroxybenzotriazole (0.47 g, 3.4 mmol) were added thereto, and the mixture was stirred for 10 minutes. Tetrahydrofuran-3-ylmethylamine (0.26 g, 2.5 mmol) was added to the mixture, and the mixture was stirred at room temperature for 18 hours. Then, water was added thereto, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.31 g of N-(tetrahydrofuran-3-ylmethyl)-5-(3-phenylpropoxymethyl)iso xazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (132)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.70-1.65(m, 1H), 1.96-1.89(m, 2H), 2.10-2.06(m, 1H), 2.59-2.56(m, 1H), 2. 69 (t, 2H), 3.46(t, 2H), 3.52(t, 2H), 3.59-3.57(m, 1H), 3.77-3.73(m, 1H), 3.94-3.79(m, 2H), 4.60(s, 2H), 6.69(s, 1H), 6.94(s, 1H), 7.20-7.16(m, 3H), 7.29-7.27(m, 2H)

184950-35-4, The synthetic route of 184950-35-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

204512-95-8, (S)-Tetrahydrofuran-3-amine hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: lambda/-(tert-Butoxycarbonyl)-lambda/-{2-r(3i?)-tetrahvdrofuran-3-ylaminolpropyUglycine (III) To a solution (0.56 M) of (35)-tetrahydrofuran-3-amine.etaCl (prepared as described in HeIv. CHm. Acta 2000, 53, 1825-1845) in DCE were added N-(tert-butoxycarbonyl)-N-(2- oxopropyl)glycine (1.3 eq), DIPEA (1 eq), NaBH(OAc)3 (2 eq), cat. AcOH and cat. NaOAc. Reaction mixture was irradiated at MW for 20 min at 1200C. DCE was removed under reduced pressure and the residue purified by filtration on silica gel eluting of the desired intermediate with EtOAc. Evaporation of the organic solvent yielded (III). MS (ES) C14H26N2O5 requires: 302, found: 303 (M+H)+., 204512-95-8

204512-95-8 (S)-Tetrahydrofuran-3-amine hydrochloride 18664284, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/63244; (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.104227-71-6,(S)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

To a solution of the compound obtained in Referential Example 194 (0.87 g) in tetrahydrofuran (20 mL) was added dropwise lithium bis(trimethylsilyl)amide (as 1M tetrahydrofuran solution, 8.65 mL) at -78C, and the thus-obtained mixture was stirred for 30 minutes. Subsequently, a solution of p-toluenesulfonyl azide (1.02 g) in tetrahydrofuran (10 mL) was added thereto, followed by stirring for 5 minutes, and after trimethylchlorosilane (1.7 mL) was added thereto, the thus-obtained mixture was gradually brought back to room temperature while being stirred. After the reaction mixture was stirred for 2 hours, the mixture was diluted with diethyl ether, and the diluted mixture was washed with 10% aqueous HCl, 5% saturated aqueous sodium hydrogencarbonate, and saturated brine, followed by drying over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 4:1), to thereby give the title compound (0.62 g).1H-NMR(CDCl3) delta:1.46(9H, s), 4.09(1H, dt, J=15.3, 7.6Hz), 4.12-4.23(1H, m), 4.37-4.50(1H, m), 4.54(1H, dd, J=9.0, 7.6Hz), 4.81-4.90(1H, m).

104227-71-6, 104227-71-6 (S)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbamate 10943528, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1577301; (2005); 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.124391-75-9,(S)-(Tetrahydrofuran-3-yl)methanol,as a common compound, the synthetic route is as follows.

Example 64A 3-(tosylmethyl)tetrahydrofuran To a solution of (tetrahydrofuran-3-yl)methanol (1.0 g, 9.8 mmol) in CH2Cl2 (5 mL) and triethylamine (1.98 g, 19.6 mmol) was added p-toluenesulfonyl chloride (2.8 g, 14.7 mmol) in portions over 15 minutes. The mixture was stirred at ambient temperature for 12 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2*10 mL) The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. MS (DCI/NH3) m/z 257 (M+H)+.

124391-75-9, The synthetic route of 124391-75-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; US2008/153883; (2008); 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.1679-47-6,3-Methyldihydrofuran-2(3H)-one,as a common compound, the synthetic route is as follows.

Step 1: Preparation of 4-hydroxy-1-(2-chloro-4-methoxyphenyl)-2-methylbutan-1-one To a 1.0 L, 3-neck round bottom flask, equipped with a mechanical stirrer and an internal thermometer, was added a solution of 4-bromo-3-chloroanisole (12.0 g, 54.0 mmol) in 350 mL of THF under nitrogen. The solution was cooled to -85 C. with a MeOH/liquid nitrogen bath. To this solution was added t-BuLi (72.0 mL, 1.6 M in pentane, 122 mmol) slowly followed by the addition of a solution of alpha-methyl-gamma-butyrolactone (9.25 g, 92.0 mmol) in THF (30.0 mL). The internal temperature was controlled <-80 C. After 1 h stirring at <-80 C., the reaction mixture was quenched with saturated NH4Cl solution and warmed to room temperature. Water and EtOAc were added and separated. The aqueous layer was extracted with EtOAc (2*). The combined organic solutions was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (E:H, 1:3) to give 10.4 g (79%) of brown oil as the title compound: 1H NMR (400 MHz, CDCl3) delta7.53 (d, J=8.6 Hz, 1H), 6.97 (d, J=2.4 Hz, 1H), 6.85 (dd, J=8.6, 2.4 Hz, 1H), 3.88 (s, 3H), 3.77-3.69 (m, 2H), 3.64-3.56 (m, 1H), 2.16-2.07 (m, 1H), 1.76-1.67 (m, 1H), 1.23 (d, J=7.0 Hz, 3H); MS (EI) m/z 241.16 (M+-H). 1679-47-6, As the paragraph descriping shows that 1679-47-6 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US2007/224636; (2007); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,453-20-3

3-Hydroxytetrahydrofuran (4.4 g, 50 mmol) was dissolved in dichloromethane (50 mL) under ice-cooling,Triethylamine (7.6 g, 75 mmol) was added and stirred for 10 min,Methylsulfonyl chloride (6.3 g, 55 mmol) was slowly added dropwise,After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour,Washed with saturated aqueous sodium chloride solution (50 mL)The organic phase was concentrated under reduced pressure to give 8.8 g of crude product.

The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shandong Xuanzhu Pharma Co., Ltd.; Wu, Yongqian; (38 pag.)CN104788412; (2017); B;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

184950-35-4, (Tetrahydrofuran-3-yl)methanamine hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Tetrahydrofuran-3-ylmethylamine hydrochloride (0.20 g, 1.44 mmol) And triethylamine (0.15 g, 1.44 mmol) Was added to chloroform (amylene added product) (6 mL). To the mixture, At room temperature 5-cyclopentylmethoxymethyl isoxazole-3-carboxylic acid (0.27 g, 1.20 mmol), 1-Hydroxybenzotriazole (0.02 g, 0.12 mmol) And 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.28 g, 1.44 mmol) After stirring for 5 hours, Dilute hydrochloric acid was added, It was extracted twice with chloroform. The organic layer was washed with saturated sodium bicarbonate water, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography , The following formulaIndicated by N- (tetrahydrofuran-3-ylmethyl) -5-cyclopentylmethoxymethyl isoxazole-3-carboxamide (Hereinafter referred to as amide compound (131)) 0.33 g was obtained., 184950-35-4

The synthetic route of 184950-35-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
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.42417-39-0,3-Aminodihydrofuran-2(3H)-one hydrochloride,as a common compound, the synthetic route is as follows.

Under ice bath conditions, 20 g of the amination product white solid was mixed with tetrahydrofuran and water, sodium carbonate was added thereto, and 30 g of benzyl chloroformate was slowly added dropwise to the reaction for half an hour, and then returned to room temperature and then continued. After reacting for 2 hours, the solvent was distilled off under reduced pressure, the pH was adjusted to acidity, and extracted with dichloromethane to give a crude compound of formula IV.Filtration of the product colorless oily liquid 13.54g, yield 90%.

42417-39-0, 42417-39-0 3-Aminodihydrofuran-2(3H)-one hydrochloride 445963, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; Wuhan Institute of Technology; Jia Lihui; Chen Yunfeng; Chen Changan; (10 pag.)CN109232644; (2019); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem