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

HRID 2109743

反応式

HRID 2109743 の反応式
[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]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 57634136tert-butyl (2S,3S)-1-(tert-butyldimethylsilyloxy)-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dfa1fc0c9b33474caafc931e2e07b0d5
出典データセット
uspto-grants-2009_04
特許番号
US07514566B2

関連ノート

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