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

HRID 361565Notes

Reaction equation

HRID 361565 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:15](=[O:16])[C@H:14]3[CH2:17][CH2:18][CH2:19][C@H:13]3[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1)([O-])=O.CO>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:15](=[O:16])[C@H:14]3[CH2:17][CH2:18][CH2:19][C@H:13]3[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 54563031(3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 53680008(3aR*,10aS*)-9-(4-Aminobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(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.

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-45d5e0dc59644930ad972f38f8a0c67c
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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