Hydrochloric Acid → HCID 54305707, compound

HRID 975649Notes

Reaction equation

HRID 975649 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si](C(C)(C)C)(C)C)[CH2:13][C@H:12]1[CH:24]=[CH:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C[O-].[Na+].CO>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[CH:24]=[CH:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23694274Sodium methanolate methanolHCID 57263621HCID 57263621, compound

Product 1

HCID 54305707HCID 54305707, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-[2-(1-methylimidazol-2-yl)vinyl]pyrrolidine (11.97 g) in methanol (80 ml) was added conc. hydrochloric acid (4.79 ml) at ambient temperature with stirring and the mixture was allowed to stand overnight at the same temperature. To the reaction mixture was added 28% sodium methoxide-methanol solution (11.4 ml) under ice-cooling with stirring and the resulting insoluble material was filtered off. The filtrate 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 (9:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-benzyloxycarbonyl-4-hydroxy-2-[2-(1-methylimidazol-2-yl)vinyl]pyrrolidine (5.47 g).

Workup

  1. temperaturecooling
  2. stirringwith stirring
  3. filtrationthe resulting insoluble material was filtered off
  4. customThe filtrate was evaporated in vacuo
  5. customto give a residue
  6. customThe residue was chromatographed on silica gel (200 g)
  7. washeluting with a mixture of chloroform and methanol (9:1, V/V)
  8. additionThe fractions containing the desired compound
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-7637812b60a240278f8dd93b90287b74
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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