Pyridine → HCID 131729156, compound

Participants

Reaction Conditions

Reaction Steps

Acetic anhydride (0.85 mL, 9.012 mmol) was added at 0° C. to a mixture of racemic trans 3-hydroxymethyl-cyclohexyl-carbamic acid tert-butyl ester (1.69 g, 7.37 mmol) and pyridine (0.78 mL, 9.646 mmol) in 20 mL of DCM. The resulting mixture was stirred at 0° C. to RT overnight and then at 50° C. for 4 hours before being cooled to RT and partitioned between DCM and aqueous 1M HCl. The aqueous layer was back extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated to give 2 g of racemic trans acetic acid 3-tert-butoxycarbonylamino-cyclohexylmethyl ester (>95% yield).

Provenance & Evidence