Triphenylphosphine → N-BOC-3-(S)-thioacetoxy-piperidine

Participants

Reaction Steps

A solution of 2.2 g of N—BOC-3-(R)-hydroxy-piperidine in 10 ml of THF is added under argon and 1 ml of thiolacetic acid to a solution of 3.4 g of triphenylphosphine and 2.65 ml of azadicarbonic acid-isopropylate in 10 ml of THF. The mixture obtained is kept for 18 hours at 70°, solvent is evaporated and the evaporation residue obtained is subjected to chromatography. N—BOC-3-(S)-thioacetoxy-piperidine is obtained. 1H-NMR (CDCl3): 3.78 (dd,1H,NCH2CHS, J=3.1 Hz, J=13.3 Hz), 3.5-3.6 (m,2H, CHSC═O, NCH2CH2), 2.32(s,3H,SC═OCH3),1.46(s,9H, tert.butyl)

Provenance & Evidence