HCID 54238483, compound → HCID 136401073, compound

HRID 1596342Notes

Reaction equation

HRID 1596342 reaction equation
C12CCC(CC1)CN(C(C[N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([CH2:24][CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[N:16][CH:15](NC(OCC3C=CC=CC=3)=O)[C:14]1=[O:42])=O)C2>CO.[OH-].[OH-].[Pd+2]>[CH:25]1([CH2:24][C:17]2[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:13][C:14](=[O:42])[CH2:15][N:16]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 1

HCID 54238483HCID 54238483, compound

Product 1

HCID 136401073HCID 136401073, compoundYield 167.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-3-benzyloxycarbonylamino-5-cyclohexylmethyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (0.396 g) in methanol (15 ml) was added Pearlman's catalyst (0.111 g). The mixture was stirred under H2 atmosphere over night. The catalyst was filtered off by suction filtration on Celite®. The filtrate was concentrated in vacuo to give (3RS)-3-amino-1-[(3-azalicyclo[3.2.2]non-3-yl)carbonylmethyl]-5-cyclohexylmethyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (0.298 g), which was used in a following reaction step without further purification.

Workup

  1. filtrationThe catalyst was filtered off by suction filtration on Celite®
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5c6d949cd41e4dbfb67bf24828ebd0d1
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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