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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 361565Generated: October 27, 2026

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

https://huagongshe.com/reaction/361565

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
Reactant(3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneHCID 54563031—
CatalystPalladiumHCID 23938—
SolventTetrahydrofuranHCID 8028—
Product(3aR*,10aS*)-9-(4-Aminobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneHCID 5368000871%

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-on-carbon (hydrous) (0.5 g) were suspended in THF (15 mL)-methanol (15 mL) and the suspension was stirred under hydrogen at room temperature for 4.5 hours. The catalyst was then filtered off and the filtrate was concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to provide 3.27 g (yield 71%) of the title compound. m.p. 149.1°-149.6° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05866567
Source datasetuspto-grants-1999_02
ORD IDord-45d5e0dc59644930ad972f38f8a0c67c
Source noteuspto-grants-1999_02