Sodium Cyanide → HCID 14830192, compound

HRID 1088255Notes

Reaction equation

HRID 1088255 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26]I)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C-:30]#[N:31].[Na+]>CN(C)C=O.O>[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26][C:30]#[N:31])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 14830190HCID 14830190, compound

Product 1

HCID 14830192HCID 14830192, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-iodomethyl-4-benzoyloxypyrrolidine (5.24 g) was dissolved in 26 ml of dry dimethylformamide, and 539 mg of sodium cyanide was added thereto, followed by stirring at room temperature for 24 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography to give (2R,4R)-1-(p-nitrobenzyloxycarbonyl)-2-cyanomethyl-4-benzoyloxypyrrolidine

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-41e39a7fee144531857d503712f26ce4
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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