(2S)-1-(2-nitrobenzoyl) proline methyl ester → (S)-(+)-2,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

HRID 1976226Notes

Reaction equation

HRID 1976226 reaction equation
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O.[H][H]>CO.[C].[Pd]>[CH2:8]1[C@H:4]2[C:3](=[O:2])[NH:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:19])[N:5]2[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 11747872(2S)-1-(2-nitrobenzoyl) proline methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 677114(S)-(+)-2,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dioneYield 76.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6.4 g of (2S)-1-(2-nitrobenzoyl) proline methyl ester in 250 ml of methanol, there was added 1.5 g of a 10% palladium-carbon catalyst and then the resulting mixture was stirred at room temperature for 6 hours in a hydrogen gas atmosphere. The catalyst present in the reaction solution was filtered off and the filtrate was concentrated under reduced pressure to give 3.8 g (yield 75.2%) of the title compound as white crystals.

Workup

  1. filtrationThe catalyst present in the reaction solution was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c58be133ec994acfa09e78bd509e4166
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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