四氢呋喃 → tert-butyl (2S,3S)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

HRID 661069笔记

反应方程式

HRID 661069 反应方程式
[Si]([O:8][CH2:9][C@@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[CH3:12])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>CCOCC>[OH:8][CH2:9][C@@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@H:11]([C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)[CH3:12]

参与物

5

反应物 3

HCID 8028四氢呋喃HCID 2724141四丁基氟化铵HCID 57634136tert-butyl (2S,3S)-1-(tert-butyldimethylsilyloxy)-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

产物 1

HCID 57634081tert-butyl (2S,3S)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

试剂、催化剂与溶剂 1

HCID 3283乙醚溶剂

实验过程

To tert-butyl (2S,3S)-1-(tert-butyldimethylsilyloxy)-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (2000 mg, 4.5 mmol) in 25 mL ether at 0° C. was added 1.0 M tetrabutylammonium fluoride in THF (8.9 mL, 8.9 mmol). After the addition, the ice-bath was taken away. The reaction progress was monitored by TLC. After 60 minutes, the solvent was evaporated and 100 mL diethyl ether was added. The organic layer was washed with water and brine solution, and then dried over sodium sulfate. The crude product was then chromatographed eluting with 30% EtOAc in hexane. After removing the solvent, the desired product was obtained as a white solid (1.25 g, 84%). 1H NMR (400 MHz, CD3OD) δ ppm 1.26-1.31 (m, 9H) 1.34 (d, J=7.04 Hz, 3H) 3.02-3.13 (m, 1H) 3.61-3.67 (m, 2H) 3.75 (dd, J=8.71, 4.60 Hz, 1H) 7.44 (d, J=8.02 Hz, 2H) 7.57 (d, J=8.22 Hz, 2H).

后处理

  1. additionAfter the addition
  2. customthe solvent was evaporated
  3. addition100 mL diethyl ether was added
  4. washThe organic layer was washed with water and brine solution
  5. dry with materialdried over sodium sulfate
  6. customThe crude product was then chromatographed
  7. washeluting with 30% EtOAc in hexane
  8. customAfter removing the solvent

来源与证据

ORD记录
ord-3d7064f5242b415b8aeb4b59d3a28e6a
来源数据集
uspto-grants-2011_12
专利号
US08084479B2

反应笔记

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