[(1S,5S)-3-[(1R)-1-Phenylethyl]-4-thioxo-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester → [(1S,5S)-3-[(1R)-1-Phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester

HRID 1917363Notes

Reaction equation

HRID 1917363 reaction equation
[C:1]([O:5][C:6]([C@@:8]12[CH:15]=[CH:14][CH2:13][C@@H:12]1[C:11](=S)[N:10]([C@@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Ni]>[C:1]([O:5][C:6]([C@@:8]12[CH:15]=[CH:14][CH2:13][C@@H:12]1[CH2:11][N:10]([C@@H:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:18])[CH2:9]2)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86664651[(1S,5S)-3-[(1R)-1-Phenylethyl]-4-thioxo-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester

Product 1

HCID 67490892[(1S,5S)-3-[(1R)-1-Phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl esterYield 65.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

[(1S,5S)-3-[(1R)-1-Phenylethyl]-4-thioxo-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester (88.2 mg, 0.27 mmol) was dissolved in ethanol. Raney nickel was added, and the mixture was stirred for one hour. The catalyst was removed by filtration, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (10% ethyl acetate/hexane) to give 55.4 mg of the title compound as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-743a60de50e447feaaa2cd3fd5036b17
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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