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

HRID 356149

Reaction equation

HRID 356149 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:15](=[O:16])[CH:14]3[CH2:17][CH2:18][CH2:19][C:13]3=[N:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(OCC)(=O)C.C(OCC)C>[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-:3])=[O:2]

Participants

3

Reactant 1

HCID 701129649-(4-Nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 54563031(3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 46%

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

Using 9-(4-nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one, synthesis was conducted by substantially the same procedure as in Working Example 24. The compound thus synthesized was purified by silica-gel column chromatography to afford the titled compound (yield 46%), m.p. 154°-155° C. (ethyl acetate-diethyl ether).

Workup

  1. customThe compound thus synthesized
  2. customwas purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-e91cc399ece34505a70e19a5297a17d7
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Linked notes

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