Triphenylphosphine → HCID 66570330, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 3-(hydroxymethyl)-1-piperidinecarboxylate (Preparation 52, 1.0 g, 5 mmol) in benzene (40 ml) under nitrogen was added triphenyl phosphine (1.44 g, 5.5 mmol). Diethyl azodicarboxylate (0.86 ml, 5.5, mmol) in benzene (4 ml) was added dropwise and the reaction mixture was stirred for 5 min. 2-mercapto pyridine (0.61 g, 5.5 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture washed with sodium hydroxide (1M), water, and saturated brine. The organic extracts were dried (Na2SO4) and concentrated to an oil which was purified by flash chromatography on silica gel eluting with dichloromethane:ethyl acetate (9:1). The title compound was obtained as an oil (1.0 g, 65%).

Provenance & Evidence