Hydrochloric Acid → HCID 53646177, compound

HRID 975651Notes

Reaction equation

HRID 975651 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH:21]=[CH:22][C:23]1[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=1)=[O:10])[C:2]1C=CC=C[CH:3]=1.Cl.[H][H]>[Pd].CO.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH2:13][C@H:12]1[CH2:21][CH2:22][C:23]1[N:24]([CH3:28])[CH:25]=[CH:26][N:27]=1)=[O:10])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 54062624HCID 54062624, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53646177HCID 53646177, compoundYield 113.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2-[2-(1-methylimidazol-2-yl)vinyl]pyrrolidine (5.70 g), conc. hydrochloric acid (2.34 ml) and 10% palladium on carbon (50% wet) (3.0 g) in methanol (120 ml) was stirred under atmospheric pressure of hydrogen at ambient temperature for 4 hours. The catalyst was filtered off and the filtrate was concentrated in vacuo. The resulting residue was dissolved in a mixture of tetrahydrofuran (60 ml) and water (60 ml). To solution was added dropwise a solution of allyloxycarbonyl chloride (1.94 ml) in tetrahydrofuran (5 ml) keeping the pH 8-10 with 4N sodium hydroxide under ice-cooling and then the mixture was stirred at the same temperature for 1 hour. The reaction mixture was concentrated in vacuo to give a residue. The residue was dissolved in ethyl acetate (100 ml) and then the solution was washed twice with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with 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-2-[2-(1-methylimidazol-2-yl)ethyl]-4-methanesulfonyloxypyrrolidine (5.69 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in a mixture of tetrahydrofuran (60 ml) and water (60 ml)
  4. additionTo solution was added dropwise a solution of allyloxycarbonyl chloride (1.94 ml) in tetrahydrofuran (5 ml)
  5. temperaturecooling
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customto give a residue
  8. washthe solution was washed twice with saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated in vacuo
  11. customThe resulting residue was chromatographed on silica gel (150 g)
  12. washeluting with chloroform and methanol (19:1, V/V)
  13. additionThe fractions containing the desired compound
  14. customwere collected
  15. customevaporated in vacuo

Sources & evidence

ORD record
ord-f80cf3023049493eb667942596b64452
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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