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

HRID 52254

反応式

HRID 52254 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-8df59e71b6e344ab8673f6d61050e653
出典データセット
uspto-grants-1997_04
特許番号
US05616612

関連ノート

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