Methanol → (2S,4R)-4-methanesulfonyloxy-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine

HRID 1650857Notes

Reaction equation

HRID 1650857 reaction equation
[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:8]([C:24]([N:26]2[CH2:30][CH2:29][NH:28][C:27]2=[O:31])=[O:25])[CH2:7]1)(=[O:4])=[O:3].CO.[H][H]>[Pd].O1CCCC1>[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:24]([N:26]2[CH2:30][CH2:29][NH:28][C:27]2=[O:31])=[O:25])[CH2:7]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 15056143(2S,4R)-4-methanesulfonyloxy-1(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 18639279(2S,4R)-4-methanesulfonyloxy-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidineYield 81.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (30 g), 10% palladium on carbon (10 g), methanol (300 ml) and tetrahydrofuran (150 ml) was stirred for 5 hours under atmospheric pressure of hydrogen at ambient temperature. After the catalyst was filtered off, the filtrate was evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (250 g) eluting with a mixture of chloroform and methanol (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-4-methanesulfonyloxy-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (14.92 g).

Workup

  1. filtrationAfter the catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customto give a residue
  4. customThe residue was chromatographed on silica gel (250 g)
  5. washeluting with a mixture of chloroform and methanol (9:1 V/V)
  6. additionThe fractions containing the desired compound
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c7f6a5bdf3f434ea6c185c341c450ba
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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