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

HRID 356199Notes

Reaction equation

HRID 356199 reaction equation
[N+:1]([C:4]1[CH:39]=[CH:38][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[N:12]([C:20](=[O:33])[CH2:21][N:22]3[C:26](=[O:27])[C:25]4=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]4[C:23]3=[O:32])[C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]2=3)=[CH:6][CH:5]=1)([O-])=O>CO.[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][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[N:12]([C:20](=[O:33])[CH2:21][N:22]3[C:23](=[O:32])[C:24]4=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]4[C:26]3=[O:27])[C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]2=3)=[CH:38][CH:39]=1

Participants

4

Reactant 1

HCID 70113442(3aR*,10aS*)-9-(4-nitrobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 54523300(3aR*,10aS*)-9-(4-aminobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][l,4]diazepin-10(1H)-oneYield 81%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A suspension of (3aR*,10aS*)-9-(4-nitrobenzyl)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (110 mg, 0.21 mmol) and platinum oxide (20 mg) in methanol (20 mL) was stirred for 12 hours at room temperature under hydrogen atmosphere. The reaction mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure, which was crystallized from diethyl ether to give 72 mg (yield 81%) of the object compound, m.p.286°-289° C.

Workup

  1. filtrationThe reaction mixture was subjected to filtration
  2. concentrationthe filtrate was concentrated under reduced pressure, which
  3. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-24805abae9ba4084babb1e2031864c72
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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