Phosgene → HCID 67310714, compound

Participants

Reaction Steps

To a solution of tert-butyl cis-3,4-diaminopyrrolidine-1-carboxylate (the product in Intermediate 11, Step C; 140 mg) and triethylamine (0.29 mL) in dichloromethane (10 mL) was added phosgene (20% in benzene, 0.4 mL) at 0° C. and the reaction mixture allowed to warm up to room temperature. The solution was evaporated after stirring for one h and purified on a Biotage Horizon® system (silica gel, 10-20% gradient of methanol containing 10% ammonium hydroxide in dichloromethane). The tert-butyl 2-oxohexahydropyrrolo[3,4-d]imidazole-5(1H)-carboxylate obtained was dissolved in trifluoroacetic acid/dichloromethane (2 mL, 1:1) and eluted through Strata-X-C™ ion exchange resin. The desired product was eluted with a solution of concentrated ammonium hydroxide in methanol (5%) and evaporated under reduced pressure.

Provenance & Evidence