Cornforth reagent → (S)-N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-oxopropyl]-Heptanamide

HRID 52254

반응식

HRID 52254 반응식
[CH3:1][C:2]([Si:5]([C:28]1C=CC=CC=1)([C:22]1C=CC=CC=1)[O:6][CH2:7][CH:8]([NH:13][C:14](=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:9](O)[CH2:10]C)([CH3:4])[CH3:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:35].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C)C=O.O>[CH3:4][C:2]([Si:5]([CH3:22])([CH3:28])[O:6][CH2:7][C@@H:8]([NH:13][C:14](=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:9][CH:10]=[O:35])([CH3:1])[CH3:3]

참가 물질

5

반응물 2

HCID 2724130Cornforth reagentHCID 54199636N-[1-[[[(1,1-Dimethylethyl)diphenylsilyl]oxy]methyl]-2-hydroxybutyl]Heptanamide

생성물 1

HCID 54133266(S)-N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-oxopropyl]-Heptanamide수율 81.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of (10c), (2.30 g, 6.94 mmol) and pyridinium dichromate (10.62 g, 28.2 mmol) in 20 mL of N,N-dimethylformamide is stirred under argon for 18 h. The reaction mixture is diluted with 100 mL of water and extracted with ethyl acetate (3×40 mL). The organic layer is separated, washed with water and brine, dried and evaporated to give 1.87 g of a residual brown liquid. The liquid is purified by chromatography using 1:6 ethyl acetate/hexane to give 997 mg of the desired product as an oil. NMR δ0.83 (S, 9H), 1.61 (m, 2H), 2.22 (t, 2H), 2.23 (s, 3H), 3.82 (dd, 1H), 4.09 (dd, 1H), 4.57 (m, 1H), 6.42 (brd, 1H); MS (FAB) m/z 330 (M+H calc'd for C17H36NO3Si 330).

후처리

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. customThe organic layer is separated
  3. washwashed with water and brine
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-8df59e71b6e344ab8673f6d61050e653
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616612

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