4-Methylmorpholine → benzyl N-[1-(hydroxymethyl)cyclohexyl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(benzyloxycarbonylamino)cyclohexane-1-carboxylic acid (4.16 g, 15.0 mmol) and N-methylmorpholine (1.81 mL, 16.5 mmol) in DME (15 mL) at 4° C. was slowly added isobutyl chloroformate (2.14 mL, 16.5 mmol) and the reaction mixture was stirred for 5 min, then filtered into a pre-cooled (4° C.) flask. Sodium borohydride (0.85 g, 22.5 mmol) in water (7 mL) wag added followed immediately by water (500 mL). The reaction was then warmed to 20° C. and stirred for 30 min. The reaction mixture was extracted with CH2Cl2 and concentrated under reduced pressure to yield 1-(benzyloxycarbonylamino)-1-(hydroxymethyl)cyclohexane (4.0 g, 100%): TLC (25% EtOAc/hex) Rf0.11.

Provenance & Evidence