Benzyl chloroformate → Benzyl 4-(2-hydroxyethyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 3-1 (Aldrich) (25 g, 0.94 mol) in THF (400 mL) was treated with diisopropylethylamine (67 mL, 0.388 mol) and cooled to 0° C. under argon. Benzylchloroformate (27.6 mL, 0.194 mol) was added and the reaction was allowed to warm to room temperature. The reaction was concentrated, the residue was diluted with Et2O (300 mL), washed with water, 10% KHSO4 solution and brine, dried (MgSO4), filtered and evaporated to give 3-2 as an oil. Rf (35% EtOAc/Hexanes) 0.08 1H NMR (300 MHz, CDCl3) δ 7.38 (s, 5H), 5.13 (s, 2H), 4.18 (b, 2H), 3.7 (dd, 2H), 2.8 (bt, 2H), 1.78 (bd, 2H), 1.5 (m, 2H), 1.4 (m, 1H), 1.2 (m, 2H).

Provenance & Evidence