(Triphenylphosphoranylidene)acetonitrile → tert-butyl (1S,2E)-3-cyano-1-isopropyl-2-propenyl(methyl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl (1S)-1-formyl-2-methylpropyl(methyl)carbamate (WO 99/32509) (500 mg, 202 mmol) in dichloromethane (5 mL) is added (triphenylphosphoranylidene)acetonitrile (700 mg, 2.32 mmol). After 1 h additional (triphenylphosphoranylidene)acetonitrile is added (350 mg, 1.16 mmol). After 24 h the reaction mixture is concentrated in vacuo and chromatographed (silica gel, hexane/ether) to give the title compound as an oil (410 mg). Analysis for C13H22N2O2: Calc'd: C, 65.52; H, 9.3; N, 11.75. Found: C, 65.3; H, 9.05; N, 11.51. MS (ES): m/z 239.1 (M+H)

Provenance & Evidence