tert-butyl N-(3-hydroxybutyl)carbamate

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

Procedure: To a stirred solution of thionyl chloride (2.0 mL, 27.9 mmol) in acetonitrile (15 mL) cooled to −45° C. is added a solution of tert-butyl (3-hydroxybutyl)carbamate (2.1 g, 11.2 mmol) in acetonitrile (20 mL) by syringe over 10 min, keeping the internal temperature below −40° C. 4-Dimethylaminopyridine (136 mg, 1.1 mmol) is added followed by the dropwise addition of pyridine (4.5 mL, 55.8 mmol, keeping the temperature below −40° C. The addition takes 90 min. Ethyl acetate (50 mL) is added to the suspension and the mixture is filtered at −35° C. to remove the solid and the solid which is washed with EtOAc before it is discarded. The filtrates are combined, and saturated Na2HPO4 solution (20 mL) is added. The mixture is stirred vigorously for 30 min and the organic layer is separated, washed with 1M NaHSO4 to remove residual pyridine, dried (MgSO4) and concentrated to afford the title compound (2.52 g, 96%) as an oil. the internal temperature below −40° C the temperature below −40° C The addition the mixture is filtered at −35° C. to remove the solid the solid which is washed with EtOAc before it saturated Na2HPO4 solution (20 mL) is added the organic layer is separated washed with 1M NaHSO4 to remove residual pyridine dried (MgSO4) concentrated

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

Procedure: A stirred solution of thionyl chloride (2.0 mL, 27.9 mmol) in acetonitrile (15 mL) is cooled down to −45° C. and a solution of tert-butyl (3-hydroxybutyl)carbamate (2.1 g, 11.2 mmol) in acetonitrile (20 mL) is added by syringe over about 10 min, keeping the internal temperature below −40° C. Then DMAP (136 mg, 1.1 mmol) is added followed by the dropwise addition of pyridine (4.5 mL, 55.8 mmol) by syringe, keeping the temperature below −40° C. The addition takes 1.5 h. Ethyl acetate (50 mL) is added to the suspension. The mixture is filtered at −35° C. to remove the solid and the solid is washed with EtOAc before it is discarded. Then the filtrates are combined, and sat. Na2HPO4 solution (20 mL) is added. Again the mixture is stirred vigorously for 30 min. Then the organic layer is separated, washed with 1M NaHSO4 to remove residual pyridine, dried (MgSO4) and concentrated to afford the title compound as an oil (2.52 g, 96%) which is used in the next step without purification. the internal temperature below −40° C the temperature below −40° C The addition The mixture is filtered at −35° C. to remove the solid the solid is washed with EtOAc before it sat. Na2HPO4 solution (20 mL) is added Then the organic layer is separated washed with 1M NaHSO4 to remove residual pyridine dried (MgSO4) concentrated