4-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidinthione → 4-(S)-(1Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]pyrrolidine

HRID 635089Notes

Reaction equation

HRID 635089 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@H:10]2[F:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2]>O1CCCC1.[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@H:10]2[F:23])[CH2:7][CH2:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 109257164-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidinthione

Product 1

HCID 109687574-(S)-(1Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]pyrrolidineYield 86%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidinethione (6.49 g, 19.35 mmol) was dissolved in anhydrous tetrahydrofuran (150 ml), and the solution was mixed with Raney nickel (15 ml) and stirred at room temperature for 30 minutes. After removing the catalyst by celite filtration (tetrahydrofuran washing), the resulting filtrate was concentrated under reduced pressure. The thus obtained residue was dissolved in diethyl ether (200 ml), washed with 10% ammonia water (200 ml×2) and saturated brine (150 ml) in that order and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 5.08 g (86.0%) of the title compound as a colorless oil.

Workup

  1. customAfter removing the catalyst
  2. filtrationby celite filtration (tetrahydrofuran washing)
  3. concentrationthe resulting filtrate was concentrated under reduced pressure
  4. dissolutionThe thus obtained residue was dissolved in diethyl ether (200 ml)
  5. washwashed with 10% ammonia water (200 ml×2) and saturated brine (150 ml) in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-458f723ea6344b72ba37772a15202fc6
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

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