Hydrochloric Acid → HCID 67705486, compound

HRID 975631Notes

Reaction equation

HRID 975631 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[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=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[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=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 67705544HCID 67705544, compound

Product 1

HCID 67705486HCID 67705486, compoundYield 149.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-[(Z)-2-(pyridin-3-yl)vinyl]-pyrrolidine (4.70 g) in methanol (50 ml) was added conc. hydrochloric acid (2.68 ml) at ambient temperature with stirring and the mixture was allowed to stand at the same temperature for 3 hours. To the reaction mixture was added 28% sodium methoxide-methanol solution (6.20 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 (150 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-[(Z)-2-(pyridin-3-yl)vinyl]-pyrrolidine (5.20 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 (150 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-ead8409090954719a82f3ac8473e46c1
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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