Dimethyl Sulfoxide → tert-Butyl 4-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 10.7 g (84.4 mM) of oxalyl chloride in 100 ml of tetrahydrofuran was added 12.0 ml (169 mM) of dimethyl sulfoxide dropwise at −78° C. and the mixture was stirred for 5 minutes. Then, a solution of [ ]g ( mM) of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate in 100 ml of tetrahydrofuran was added dropwise and the mixture was stirred at −78° C. for 15 minutes. To this mixture was added 47.0 ml (338 mM) of triethylamine at −78° C. and the temperature was increased to room temperature. This reaction mixture was poured in water and extracted with 3 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The resulting crude tert-butyl 4-formylpiperidine-1-carboxylate was not purified but used as it was in the next reaction.

Provenance & Evidence