Triethylamine → Benzyl 3-hydroxypyrrolidine-1-carboxylate

Participants

Reaction Steps

To a stirring solution of 3-pyrrolidinol (1780 mg, 20.4 mmol, Aldrich) and dry triethylamine (4130 mg, 40.9 mmol, Aldrich) in dry CH2Cl2 (120 mL) at 0° C. was benylchloroformate (3.83 mg, 22.5 mmol, Aldrich). The reaction was allowed to warm to room temperature and stirred for 16 h. The reaction was quenched by the addition of 1M aqueous HCl (100 mL) and EtOAc (200 mL). The organic layer was separated, washed with brine, dried over Na2SO4, and conc. in vacuo to a colorless oil. The oil was purified by flash chromatography (SiO2, hex:EtOAc, 2:1) to yield of pure N-(benzyloxycarbonyl)-3-pyrrolidinol. MS (ESI) 222 (M+H).

Provenance & Evidence