Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Benzyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of N-benzyloxycarbonyl-4-piperidinone (5.0 g, 21.4 mol) and methyl (triphenylphosphoranylidene)acetate (10.0 g, 30.0 mmol) in benzene (100 mL) was heated at 75° C. for 48 h. The reaction was concentrated, diluted with ether, the precipitate filtered off, and the rinsate concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 20 to 60% ethyl acetate:hexanes to give the title compound (5.25 g). MS: m/z=290.1 (M+1).

Provenance & Evidence