Triphenylphosphine → (4S)-4-acetylthio-2-pyrrolidone

HRID 1082745Notes

Reaction equation

HRID 1082745 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C:4](=O)[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:39](O)(=[S:41])[CH3:40]>O1CCCC1>[C:2]([C@@H:3]1[CH2:4][NH:5][C:39](=[S:41])[CH2:40]1)(=[O:1])[CH3:6]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 185505(R)-(+)-4-Hydroxy-2-pyrrolidinoneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178418634HCID 178418634, compound

Product 1

HCID 86746170(4S)-4-acetylthio-2-pyrrolidone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 300 ml of tetrahydrofuran was suspended 4.5 g of (4R)-4-hydroxy-2-pyrrolidone, 23.4 g of triphenylphosphine was added thereto, and the mixture was stirred for 10 minutes. Subsequently, 14 ml of diethyl azodicarboxylate was added dropwise to the reaction mixture at -10° C., and the mixture was stirred at the same temperature for 10 minutes. After 6.3 ml of thioacetic acid was added dropwise to the reaction mixture at -10° C. or lower, the mixture was stirred at the same temperature for 2 hours and the solvent was removed. The residue was crystallized from diisopropyl ether. After the crystals were removed by filtration, the filtrate was condensed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; chloroform:ethanol=98:2) to obtain 3.8 g of (4S)-4-acetylthio-2-pyrrolidone as an oily product.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at the same temperature for 10 minutes
  3. stirringlower, the mixture was stirred at the same temperature for 2 hours
  4. customthe solvent was removed
  5. customThe residue was crystallized from diisopropyl ether
  6. customAfter the crystals were removed by filtration
  7. customcondensed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (solvent; chloroform:ethanol=98:2)

Sources & evidence

ORD record
ord-2e7ea2deba554f84b1019aeb62092ffa
Source dataset
uspto-grants-1996_12
Patent number
US05589592

Reaction notes

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