Sodium Carbonate → (3aR*,10aS*)-9-[4-(Benzyloxycarbonylamino)benzyl]-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (3aR*,10aS*)-9-(4-aminobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (3.64 g, 12 mmol) in dichloromethane (15 mL) was added a solution of sodium carbonate (1.88 g, 18 mmol) in water (15 mL) at 0° C. To this mixture was added benzyl chloroformate (2.0 mL, 14 mmol) at the same temperature and the mixture was stirred at 0° C. for 15 minutes. Upon phase separation, the aqueous layer was extracted with dichloromethane and the pooled organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to provide 4.18 g (yield 79%) of the title compound. m.p. 161.7°-162.5° C.

Provenance & Evidence