Cornforth reagent → (S)-N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxopropyl]-Heptanamide

HRID 1781347Notes

Reaction equation

HRID 1781347 reaction equation
[CH3:1][C:2]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH:8]([NH:12][C:13](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:9]([OH:11])[CH3:10])([CH3:4])[CH3:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C)C=O.O>[CH3:1][C:2]([Si:5]([CH3:21])([CH3:22])[O:6][CH2:7][C@H:8]([NH:12][C:13](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:9](=[O:11])[CH3:10])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 76412708N-[1-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-hydroxypropyl]heptanamide

Product 1

HCID 53929201(S)-N-[1-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-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 δ 0.83 (s, 9 H), 1.61 (m, 2 H), 2.22 (t, 2 H), 2.23 (s, 3 H), 3.82 (dd, 1 H), 4.09 (dd, 1 H), 4.57 (m, 1 H), 6.42 (brd, 1 H); 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-2ac639f6a6d7446bbbb8b363582dbac2
Source dataset
uspto-grants-1997_05
Patent number
US05633280

Reaction notes

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