HCID 86755852, compound → HCID 54072739, compound

HRID 1954587Notes

Reaction equation

HRID 1954587 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C@@H:9]2[C@@H:13]([CH3:14])[CH2:12][N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[C:10]2=S)[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[C@@H:13]([CH3:14])[CH2:12][N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[CH2:10]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 86755852HCID 86755852, compound

Product 1

HCID 54072739HCID 54072739, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

(3S,4R)-3-(1-Ethoxycarbonylcyclopropyl)-4-methyl-1-[(S)-1-phenylethyl]-2-pyrrolidinethion (1.80 g, 5.43 mmol) was dissolved in ethanol (100 ml), and the solution was mixed with Raney nickel (10 ml) and heated under reflux for 1.5 hours. After completing the reaction, the reaction solution was filtered through celite and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in chloroform (100 ml), washed with 10% ammonia water (100 ml), water (100 ml) and saturated brine (100 ml) in that order and then dried over anhydrous sodium sulfate. After evaporating the solvent, the resulting residue was purified by silica gel column chromatography (silica gel, 160 ml; ethyl acetate:hexane=1:1), to thereby obtain 558 mg (34%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. customthe reaction
  4. filtrationthe reaction solution was filtered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in chloroform (100 ml)
  7. washwashed with 10% ammonia water (100 ml), water (100 ml) and saturated brine (100 ml) in that order
  8. dry with materialdried over anhydrous sodium sulfate
  9. customAfter evaporating the solvent
  10. customthe resulting residue was purified by silica gel column chromatography (silica gel, 160 ml; ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-f1b90cc860bf43dd84006ea5f411ff2c
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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