Diethyl Ether → Tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 132 (0.96 g, 3.9 mmol) in ether (20 mL) at ambient temperature was treated with LiBH4 (0.34 g, 15.8 mmol) then heated to 55° C. After 45 min at 55° C., the cooled reaction was quenched with 5% KHSO4 (10 mL) and then diluted with EtOAc. The organic phase was washed with 5% KHSO4 and brine, dried (MgSO4), and concentrated to give 133 (0.79 g) as a colorless oil. Rf 0.46 (silica, EtOAc). 1H NMR (300 MHz, CDCl3) δ 4.04 (m, 2H), 3.70-3.50 (m, 4H), 2.63 (m, 1H), 1.83 (m, 2H), 1.44 (s, 9H). ##STR58##

Provenance & Evidence