Acetic Acid → HCID 86719580, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 3-(3-amino-5-(methoxycarbonyl)-4-methylphenoxy)azetidine-1-carboxylate (0.90 g, 2.67 mmol) and tert-butyl (4-oxocyclohexyl)carbamate (0.741 g, 3.47 mmol) in dichloroethane (10 mL) was added acetic acid (0.96 g, 16.1 mmol) and the mixture stirred at room temperature for 20 minutes. Then sodium triacetoxyborohydride (1.7 g, 8.0 mmol) was added at 0° C. and the reaction stirred at room temperature for 2 h. On completion, the reaction was quenched with aqueous sodium bicarbonate, the organic phase separated and the aqueous phase extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure and the crude material purified by column chromatography to afford the title compound (0.9 g, 63%) as a mixture of cis/trans isomers.

Provenance & Evidence