Pyridine → HCID 67235477, compound

Participants

Reaction Steps

To a stirred solution of thionyl chloride (5.4 g, 45.4 mmol) in acetonitrile (25 mL) cooled to −45° C. is added a solution of tert-butyl (3-hydroxy-2-methylbutyl)carbamate (3.7 g, 18.1 mmol) in acetonitrile (35 mL) by syringe over about 15 min, keeping the internal temperature below −40° C. When the addition is completed, solid 4-dimethylamino pyridine (222 mg, 1.8 mmol) is added in one portion followed by pyridine (7.3 mL, 90.8 mmol), keeping the temperature below −40° C. The mixture is stirred at −40° C. to −35° C. for 1 h. Ethyl acetate (100 mL) is added and the mixture is filtered at −35° C. The solid is washed with EtOAc and discarded. To the filtrate is added saturated Na2HPO4 solution (20 mL) and the mixture is stirred vigorously for 3 h. The organic layer is separated, washed with 1M NaHSO4, dried (MgSO4) and concentrated to afford the title compound (4.4 g) which is used in the next step without purification.

Provenance & Evidence