Water → (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-{2(5-methoxymethylimidazol-1-yl)ethyl}pyrrolidine

HRID 975704Notes

Reaction equation

HRID 975704 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:13][CH2:14][N:15]1[C:19]([CH2:20][O:21][CH3:22])=[CH:18][N:17]=[CH:16]1)=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].O>C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:9][C@H:8]1[CH2:13][CH2:14][N:15]1[C:19]([CH2:20][O:21][CH3:22])=[CH:18][N:17]=[CH:16]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53905519(2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-{2-(5-methoxymethylimidazol-1-yl)ethyl}pyrrolidine

Product 1

HCID 22870378(2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-{2(5-methoxymethylimidazol-1-yl)ethyl}pyrrolidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-{2-(5-methoxymethylimidazol-1-yl)ethyl}pyrrolidine (3.63 g) in ethyl acetate (40 ml) were added successively triethylamine (2.29 ml) and methanesulfonyl chloride (1.09 ml) with stirring under ice-cooling. The mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added water (20 ml). The organic layer was separated and washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (150 g) eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-{2(5-methoxymethylimidazol-1-yl)ethyl}pyrrolidine (3.85 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customto give a residue
  8. customThe residue was chromatographed on silica gel (150 g)
  9. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  10. additionThe fractions containing the desired compound
  11. customwere collected
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-0fb31f0d8f624e49a719f0733fe408e1
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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