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

HRID 248209Notes

Reaction equation

HRID 248209 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

(4R)-4-Hydroxy-2-pyrrolidone (4.5 g) is suspended in tetrahydrofuran (300 ml), and thereto is added triphenylphosphine (23.4 g). After stirring the mixture for 10 minutes, diethyl azodicarboxylate (14 ml) is added dropwise to the mixture below -10° C., and the mixture is stirred at the same temperature for 10 minutes. Thioacetic acid (6.3 ml) is added dropwise to the reaction mixture below -10° C., and the mixture is stirred at the same temperature for 2 hours, and the solvent is evaporated under reduced pressure. The residue is crystallized from diisopropyl ether, and the precipitate is removed by filtration. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent, chloroform : ethanol =98:2) to give (4S)-4-acetylthio-2-pyrrolidone (3.8 g) as an oil.

Workup

  1. stirringthe mixture is stirred at the same temperature for 10 minutes
  2. stirringthe mixture is stirred at the same temperature for 2 hours
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is crystallized from diisopropyl ether
  5. customthe precipitate is removed by filtration
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customthe residue is purified by silica gel column chromatography (eluent, chloroform : ethanol =98:2)

Sources & evidence

ORD record
ord-f5ade569c9b14b48a955d4914a3cf2a0
Source dataset
uspto-grants-1993_05
Patent number
US05208348

Reaction notes

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