Dimethyl Sulfoxide → HCID 20140875, compound

HRID 1252215Notes

Reaction equation

HRID 1252215 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N+:11]([C:14]1[CH:31]=[CH:30][C:17]([CH2:18][O:19][C:20]([N:22]2[CH2:27][CH2:26][CH:25]([CH2:28][OH:29])[CH2:24][CH2:23]2)=[O:21])=[CH:16][CH:15]=1)([O-:13])=[O:12].C(N(CC)CC)C>ClCCl>[N+:11]([C:14]1[CH:31]=[CH:30][C:17]([CH2:18][O:19][C:20]([N:22]2[CH2:27][CH2:26][CH:25]([CH:28]=[O:29])[CH2:24][CH2:23]2)=[O:21])=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13334363HCID 13334363, compound

Product 1

HCID 20140875HCID 20140875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (2 ml) in dry dichloromethane (50 ml) was added dropwise dry dimethyl sulfoxide (3.4 ml) at -60° C. and the resulting mixture was stirred for 10 minutes. To the mixture was added a solution of N-p-nitrobenzyloxycarbonyl-4-hydroxymethylpiperidine (5.88 g) in dry dichloromethane (40 ml) at the same temperature. After stirring for 15 minutes, triethylamine (14 ml) was added to the mixture. The reaction mixture was stirred at -60° C. for 5 minutes and at room temperature for 30 minutes, and diluted with dichloromethane. The reaction mixture was washed successively with water, dilute hydrochloric acid and again water, dried over anhydrous sodium sulfate and evaporated to give N-p-nitrobenzyloxycarbonyl-4-formylpiperidine.

Workup

  1. stirringAfter stirring for 15 minutes
  2. stirringThe reaction mixture was stirred at -60° C. for 5 minutes and at room temperature for 30 minutes
  3. washThe reaction mixture was washed successively with water, dilute hydrochloric acid and again water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-7db58ce738fd43caa70721166cc795a5
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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