Dimethyl Sulfoxide → 1-Tritylpiperidin-3-one

HRID 1272380Notes

Reaction equation

HRID 1272380 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13]1.C(N(CC)CC)C>ClCCl>[C:18]([N:14]1[CH2:15][CH2:16][CH2:17][C:12](=[O:11])[CH2:13]1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 222535813-Piperidinol, 1-(triphenylmethyl)-

Product 1

HCID 227070511-Tritylpiperidin-3-oneYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 1.7 mL (24 mmol) of DMSO in 30 mL of dichloromethane at −50° C. was added dropwise 5.5 mL (11.0 mmol) of 2.0 M oxalyl chloride solution in dichloromethane. After 10 min, a solution of 3.85 g (10.0 mmol) of 3-hydroxy-1-(triphenylmethyl)piperidine from Step A in 15 mL of dichloromethane was added dropwise. After 15 min, 7.0 mL (50 mmol) of triethylamine was added dropwise. The reaction mixture was allowed to warm to ambient temperature over 0.5 h. The mixture was diluted with dichloromethane, washed sequentially with water, 5% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine, dried over sodium sulfate and concentrated. Purification by flash chromatography (silica gel, 6% ethyl acetate/hexane) gave 1.95 g (57%) of the title compound as a white crystalline solid.

Workup

  1. waitAfter 15 min
  2. washwashed sequentially with water, 5% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by flash chromatography (silica gel, 6% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-111dead922854462a2fa667ca6caf445
Source dataset
uspto-grants-2007_04
Patent number
US07208498B2

Reaction notes

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