Sodium hydride → HCID 13334365, compound

HRID 1252214Notes

Reaction equation

HRID 1252214 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:32]([OH:35])(=[S:34])[CH3:33].[Na].C(O)(=S)C.[H-].[Na+]>CN(C)C=O.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:13][CH2:14][CH:15]([CH2:18][S:34][C:32](=[O:35])[CH3:33])[CH2:16][CH2:17]2)=[O:11])=[CH:30][CH:31]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 13334364HCID 13334364, compoundHCID 178418634HCID 178418634, compoundHCID 178477229HCID 178477229, compound

Product 1

HCID 13334365HCID 13334365, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-p-nitrobenzyloxycarbonyl-4-p-toluenesulfonyloxymethylpiperidine (3.72 g) in dry dimethylformamide (10 ml) was added to a solution of sodium thioacetic acid (1 g) prepared from thioacetic acid and sodium hydride in dry dimethylformamide (10 ml). The reaction mixture was stirred at room temperature for 4 hours, diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give a residue which was then purified by silica gel column chromatography to give N-p-nitrobenzyloxycarbonyl-4-acetylthiomethylpiperidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto give a residue which
  6. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-42fca22a84a844f3842916fd3f843dc6
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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