HCID 67415713, compound → HCID 67416430, compound

HRID 1803612Notes

Reaction equation

HRID 1803612 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]#[N:23])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>N.CCO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH:14]([CH2:13][N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:22][NH2:23])[CH2:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67415713HCID 67415713, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67416430HCID 67416430, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

To a solution of 5-(2-cyano-phenyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (150 mg, 0.48 mmol) in NH3/EtOH (2M, 10 mL) was added Raney Nickel (3 mL slurry in water). The atmosphere was exchanged with hydrogen via balloon and the mixture was allowed to stir for 2.5 h. After this time the mixture was filtered through celite and concentrated to yield the title compound (140 mg). m/z (M+1) 318.29.

Workup

  1. filtrationAfter this time the mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9e098bda7ed7416588765406de073907
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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