(2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine → (2S,4S)-4-acetylthio-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine

HRID 1590506Notes

Reaction equation

HRID 1590506 reaction equation
CS(O[C@H:6]1[CH2:10][N:9]([CH3:11])[C@H:8]([CH2:12][N:13]2[CH2:17][CH2:16][NH:15][C:14]2=[O:18])[CH2:7]1)(=O)=O.[C:19]([O-:22])(=[S:21])[CH3:20].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[C:19]([S:21][C@@H:6]1[CH2:10][N:9]([CH3:11])[C@H:8]([CH2:12][N:13]2[CH2:17][CH2:16][NH:15][C:14]2=[O:18])[CH2:7]1)(=[O:22])[CH3:20]

Participants

4

Reactant 2

HCID 15056170(2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidineHCID 178477078HCID 178477078, compound

Product 1

HCID 18639285(2S,4S)-4-acetylthio-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidineYield 79.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (2.50 g) and tetra-n-butylammonium thioacetate (4.16 g) in acetonitrile (70 ml) was stirred at 50°-60° C. for 4 hours. The reaction mixture was evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (200 g) eluting with a mixture of chloroform and methanol (20:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-acetylthio-1-methyl-2-(2-oxoimidazolidin-1-yl)methylpyrrolidine (1.84 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto give a residue
  3. customThe residue was chromatographed on silica gel (200 g)
  4. washeluting with a mixture of chloroform and methanol (20:1 V/V)
  5. additionThe fractions containing the desired compound
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-bb3672d1f9b24f67985ffde8f224d258
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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