HCID 53793574, compound → HCID 53867236, compound

HRID 2371402Notes

Reaction equation

HRID 2371402 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[CH2:24][C:25]#[N:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.Cl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[CH2:24][C:25]#[N:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 53793574HCID 53793574, compound

Product 1

HCID 53867236HCID 53867236, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,4R)-1-benzyloxycarbonyl-2-cyanomethyl-4-t-butyldimethylsilyloxypyrrolidine (88 g) in methanol (450 ml), 6N hydrochloric acid (45 ml) was added, and the resultant mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with ethyl acetate, washed with aqueous sodium chloride solution and dried over magnesium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography to give (2R,4R)-1-benzyloxycarbonyl-2-cyanomethyl-4-hydroxypyrrolidine.

Workup

  1. washwashed with aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customAfter removal of the solvent
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-057ce49ba2e344f6942238acaa1031d3
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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