Pyridine → HCID 67235126, compound

Participants

Reaction Steps

To a solution of thionyl chloride (192 mL, 2.6 mol) in acetonitrile (1.0 L) at −40° C. is added dropwise a solution of tert-butyl [(3S)-3-hydroxybutyl]carbamate (200 g, 1.1 mol) in acetonitrile (2.5 L). The mixture is stirred for 10 min and 4-dimethylaminopyridine (12.9 g, 105.66 mmol) is added. After stirring for another 10 min, pyridine (427 mL, 5.3 mol) is added over 90 min, keeping the temperature below −40° C. EtOAc is added at −40° C. and the suspension is filtered to remove the solid. To the filtrate is added saturated Na2HPO4 solution and the mixture is stirred vigorously for 30 minutes at room temperature. The organic layer is separated, washed with 1M NaHSO4 solution, dried (Na2SO4) and concentrated to afford the title crude compound (250 g) as an oil which is used in the next step without purification.

Provenance & Evidence