Acetic Acid → HCID 23062736, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl N-(4-hydroxycyclohexyl)carbamate (15 g, 69.67 mmol, 1.00 equiv), acetic acid (16.7 g, 278.09 mmol, 4.00 equiv) and triphenylphosphane (73 g, 278.32 mmol, 4.00 equiv). in tetrahydrofuran (200 mL) was added diethyl azodicarboxylate (48.55 g, 278.78 mmol, 4.00 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature and then 200 mL of aqueous sodium bicarbonate solution was added. The resulting mixture was extracted with 3×100 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was triturated with 500 mL of a 1:1 mixture of ether and hexane. The solid triphenylphosphine oxide was removed by filtration. The filtrate was concentrated under vacuum and purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:15) to give 3.8 g (21%) of 4-[[(tert-butoxy)carbonyl]amino]cyclohexyl acetate as a white solid.

Provenance & Evidence