Dimethyl Sulfoxide → Ethyl 4-formylpiperidine-1-carboxylate

HRID 2266052Notes

Reaction equation

HRID 2266052 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl>[CH:12]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19773576Ethyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 14989210Ethyl 4-formylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1.2 eq oxalyl chloride (12.69 g, 0.10 mol) in dichloromethane (150 mL) was cooled to approximately −78° C. and treated dropwise, under nitrogen, with a solution of 2.4 equivalents anhydrous dimethylsulfoxide (15.63 g, 0.20 mol) in dichloromethane (50 mL). 15 min. after the addition was complete, a solution of 1.0 equivalent ethyl 4-(hydroxymethyl)-piperidine-1-carboxylate (D2) (15.60 g, 83.3 mmol) in dichloromethane (50 mL) was added dropwise. 30 minutes after the addition was complete, a solution of 3.0 eq triethylamine

Workup

  1. addition15 min. after the addition
  2. addition30 minutes after the addition

Sources & evidence

ORD record
ord-4fee894eb7754495a46d55a8160a51a8
Source dataset
uspto-grants-2010_12
Patent number
US07858635B2

Reaction notes

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