Acetic Anhydride → tert-Butyl (1R*,4R*)-4-acetamidocyclohexylcarbamate

Participants

Reaction Steps

To a cooled suspension of (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (15 g) in DCM (300 mL) was added Ac2O (10.8 mL) followed by TEA (2.19 mL), and the resulting mixture was stirred at RT for 3 h. The reaction mixture was then partitioned between DCM and water, and isopropyl amine was added to facilitate the separation. The organic layer was washed with dilute aqueous NaHCO3, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was triturated with Et2O, the solid was collected by filtration and dried under reduced pressure to afford 14.3 g of (4-acetylamino-cyclohexyl)-carbamic acid tert-butyl ester.

Provenance & Evidence