Sodium Carbonate → benzyl 3-(1-amino-5-cyano-1H-pyrrol-2-yl)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of benzyl 3-{1-[(tert-butoxycarbonyl)amino]-5-cyano-1H-pyrrol-2-yl}azetidine-1-carboxylate (800 mg, 2.02 mmol) in methanol (2.5 mL) was added a solution of 4 M HCL in dioxane (2.5 mL). The reaction was stirred (0° C.) for 15 min, then was allowed to warm to rt. After 4 h, the reaction was recooled (0° C.) and the mixture was made basic (pH 9) with slow addition of 2M aqueous Na2CO3. The mixture was allowed to warm to rt and was extracted with EtOAc (3×20 mL). The combined organics were washed with brine, dried (Na2SO4), and evaporated to afford 575 mg (96%) of the desired product, which was used without further characterization.

Provenance & Evidence