HCID 11759977, compound → HCID 21971267, compound

HRID 1954605Notes

Reaction equation

HRID 1954605 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=S)[C:10]2([F:24])[F:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(O)C.[Ni]>[CH2:1]([O:3][C:4]([C:6]1([C@@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:15])[CH2:11][C:10]2([F:24])[F:23])[CH2:7][CH2:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 11759977HCID 11759977, compound

Product 1

HCID 21971267HCID 21971267, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

4-(S)-(1Ethoxycarbonylcyclopropyl)-3,3-difluoro-1-[1-(S)-phenylethyl]-2-pyrrolidinethione (2.883 g, 8.157 mmol) was dissolved in anhydrous ethanol (80 ml), and the solution was mixed with Raney nickel (8 ml) and stirred at room temperature for 30 minutes. After removing the catalyst by celite filtration (ethanol washing), the resulting filtrate was concentrated under reduced-pressure. The thus obtained residue was dissolved in diethyl ether (150 ml), washed with 10% ammonia water (100 ml×4) and saturated brine (100 ml) in that order and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=4:1, to thereby obtain 2.540 g (96.3%) of the title compound as a colorless oil.

Workup

  1. customAfter removing the catalyst
  2. filtrationby celite filtration (ethanol washing)
  3. concentrationthe resulting filtrate was concentrated under reduced-pressure
  4. dissolutionThe thus obtained residue was dissolved in diethyl ether (150 ml)
  5. washwashed with 10% ammonia water (100 ml×4) and saturated brine (100 ml) in that order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. washeluted with an eluant of n-hexane

Sources & evidence

ORD record
ord-59a2884494444effb96c2b26249a45a5
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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