tert-butyl N-[(3R)-3-hydroxybutyl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of thionyl chloride (2.9 g, 24.3 mmol) in acetonitrile (15 mL) is cooled to −45° C. is added a solution of tert-butyl [(3R)-3-hydroxybutyl]carbamate (1.8 g, 9.7 mmol) in acetonitrile (20 mL) by syringe over 10 min, keeping the internal temperature below −40° C. 4-Dimethylaminopyridine (119 mg, 0.97 mmol) is added followed by the slow addition of pyridine (3.9 mL, 48.6 mmol), keeping the temperature below −40° C. Ethyl acetate (50 mL) is added to the suspension and the mixture at −35° C. is filtered. The solid is washed with EtOAc and the filtrates are combined. Saturated Na2HPO4 solution (20 mL) is added into the filtrates and the mixture is stirred vigorously for 30 min. The organic layer is separated, washed with 1M NaHSO4, dried (MgSO4) and concentrated to afford the title compound (2.3 g, 99%) which is used in the next step without purification. the internal temperature below −40° C the temperature below −40° C the mixture at −35° C. is filtered The solid is washed with EtOAc Saturated Na2HPO4 solution (20 mL) is added into the filtrates The organic layer is separated washed with 1M NaHSO4 dried (MgSO4) concentrated