Water → tert-Butyl 4-(benzyloxy)piperidine-1-carboxylate

Participants

Reaction Steps

Sodium hydride, 80% dispersion in oil (0.14 g, 4.8 mmoI) was added to a solution of 1-(tert-butoxycarbonyl)-4-hydroxypiperidine (1.0 g, 4.8 mmol) [prepared from 4-hydroxypiperidine and di-tert-butyl dicarbonate] in dimethylformamide (30 ml) and the mixture stirred for 30 minutes. Benzyl bromide (0.68 ml, 5.7 mmol) was added and the reaction mixture stirred overnight. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with water and brine, dried (MgSO4) and the residue after evaporation purified by flash chromatography eluting with 0-20% ethyl acetate in hexane to give 1-(tert-butoxycarbonyl)-4-benzyloxypiperidine (1.1 g, 94% ); δH (CDCl3) 1.39 (9H, s, C(CH3)3), 1.82 (2H, m, piperidinyl. H), 3.04 (2H, m, piperidinyl H), 3.59 (3H, m, piperidinyl H), 4.51 (2H, s, OCH2Ph), 7.24-7.39 (5H, m, PhH).

Provenance & Evidence