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

HRID 52254

Reaction equation

HRID 52254 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-8df59e71b6e344ab8673f6d61050e653
Source dataset
uspto-grants-1997_04
Patent number
US05616612

Linked notes

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