Dimethyl Sulfoxide → 1,1-Dimethylethyl 3-formyl-3-methyl-1-piperidinecarboxylate

HRID 412241Notes

Reaction equation

HRID 412241 reaction equation
[OH:1][CH2:2][C:3]1([CH3:16])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.CS(C)=O.CCN(CC)CC>C(Cl)Cl.CCOCC>[CH:2]([C:3]1([CH3:16])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)=[O:1]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 22258928Tert-butyl 3-(hydroxymethyl)-3-methylpiperidine-1-carboxylate

Product 1

HCID 222589171,1-Dimethylethyl 3-formyl-3-methyl-1-piperidinecarboxylateYield 86%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice water cooled solution of tert-butyl 3-(hydroxymethyl)-3-methyl-1-piperidinecarboxylate (1.5 g, 6.6 mmol) in CH2Cl2 were added DMSO (7.1 g, 91.6 mmol), Et3N (5.5 mL, 39.8 mmol), and sulfur trioxide-Pyridine complex (3.1 g, 19.9 mmol) successively. The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ether, purified by column chromatography on silica gel (hexane:ethyl acetate, 5:1-4:1) to give tert-butyl 3-formyl-3-methyl-1-piperidinecarboxylate as a colorless oil form (1.3 g, yield; 86%).

Workup

  1. custompurified by column chromatography on silica gel (hexane:ethyl acetate, 5:1-4:1)

Sources & evidence

ORD record
ord-8d50043117d5463aa1985a0dcb026fcc
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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