HCID 54377307, compound → HCID 69686722, compound

HRID 1936632Notes

Reaction equation

HRID 1936632 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C@@H:13]2[CH2:15][C@@H:14]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]1=S)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].C(O)C>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([C@H:13]2[CH2:15][C@@H:14]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 54377307HCID 54377307, compound

Product 1

HCID 69686722HCID 69686722, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To 60 ml of an ethanol solution of 4.040 g (12.19 mmol) of 1-benzyl-3-[(1R,2S)-2-t-butoxycarbonylcyclopropyl]pyrrolidine-2-thione (isomer B1) was added 20 ml of Raney nickel, followed by stirring at room temperature for 40 minutes. Any insoluble matter was removed by filtration, and the solvent was evaporated under reduced pressure. Chloroform was added to the residue, and the mixture was washed with 10% aqueous ammonia. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 2.988 g (81.3%) of the title compound as a colorless oily substance.

Workup

  1. customAny insoluble matter was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. additionChloroform was added to the residue
  4. washthe mixture was washed with 10% aqueous ammonia
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-927fc64f98f74a0ab4f1bcd77e15b6ff
Source dataset
uspto-grants-2002_05
Patent number
US06391889B1

Reaction notes

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