Sodium Cyanide → HCID 53793574, compound

HRID 2371401Notes

Reaction equation

HRID 2371401 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[CH2:24]I)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:26]#[N:27].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[CH2:24][C:26]#[N:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 15671511HCID 15671511, compound

Product 1

HCID 53793574HCID 53793574, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-iodomethyl-4-t-butyldimethylsilyloxypyrrolidine (110 g) in dry dimethylformamide (300 ml), sodium cyanide (10.29 g) was added, and the resultant mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with ethyl acetate, washed with aqueous sodium hypochlorite solution and aqueous sodium chloride solution in order 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-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. washwashed with aqueous sodium hypochlorite solution and aqueous sodium chloride solution in order
  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-5ab571c856234ab8ba348824c77e44b8
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

Loading…