Triphenylphosphine → (4S)-4-(acetylsulfanyl)pyrrolidin-2-one

HRID 1030178Notes

Reaction equation

HRID 1030178 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:21]1[CH2:25][NH:24][C:23](=[O:26])[CH2:22]1.N(C(OCC)=O)=NC(OCC)=O.[C:39]([OH:42])(=[S:41])[CH3:40]>O1CCCC1>[C:39]([S:41][CH:21]1[CH2:25][NH:24][C:23](=[O:26])[CH2:22]1)(=[O:42])[CH3:40]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1528074-Hydroxy-2-pyrrolidinoneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178418634HCID 178418634, compound

Product 1

HCID 14456882(4S)-4-(acetylsulfanyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

20-(1) 15.6 g of triphenylphosphine were added to a suspension of 3 g of 4-hydroxy-2-pyrrolidinone in 200 ml of tetrahydrofuran, and then the mixture was stirred at room temperature for 5 minutes, after which it was cooled to -20° C. A solution of 9.3 ml of diethyl azodicarboxylate in 9 ml of tetrahydrofuran was added dropwise, whilst cooling at -12° C. to -20° C., to the previous solution. The mixture was then stirred at 0°-5° C. for 5 minutes, after which it was again cooled to -20° C. 4.2 ml of thioacetic acid were then added dropwise to the mixture, whilst cooling at -18° C. to -20° C. The mixture was then warmed to 0-5° C. and stirred at that temperature for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure. The residue was purified first by column chromatography through silica gel, eluted with a 10:1 by volume mixture of ethyl acetate and methanol, and then by column chromatography through silica gel, eluted with a 2:1 by volume mixture of acetonitrile and benzene, to give 2.45 g of 4-acetylthio-2-pyrrolidinone as colorless crystals.

Workup

  1. temperatureafter which it was cooled to -20° C
  2. temperaturewhilst cooling at -12° C. to -20° C., to the previous solution
  3. stirringThe mixture was then stirred at 0°-5° C. for 5 minutes
  4. temperatureafter which it was again cooled to -20° C
  5. temperaturewhilst cooling at -18° C. to -20° C
  6. temperatureThe mixture was then warmed to 0-5° C.
  7. stirringstirred at that temperature for 2 hours
  8. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  9. customThe residue was purified first by column chromatography through silica gel
  10. washeluted with a 10:1 by volume mixture of ethyl acetate and methanol
  11. washby column chromatography through silica gel, eluted with a 2:1 by volume mixture of acetonitrile and benzene

Sources & evidence

ORD record
ord-53c68418537144af8ead58a9279c0921
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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