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

Participants

Reaction Steps

(3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (5.06 g, 15 mmol) and 10% palladium-carbon (hydrous) (0.5 g) were suspended in a mixture of tetrahydrofuran (15 mL) and methanol (15 mL). The suspension was stirred for 4.5 hours at room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was crystallized from ethyl acetate-hexane to give 3.27 g (yield 71%) of the titled compound, m.p. 149.1°-149.6° C.

Provenance & Evidence