Dimethyl Sulfide → 1-Tert-butyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

HRID 1442903Notes

Reaction equation

HRID 1442903 reaction equation
[O:1]=[O+][O-].[CH2:4]([C:7]1([C:20]([O:22][CH3:23])=[O:21])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)[CH:5]=C.ClCCl.CSC>CO>[O:1]=[CH:5][CH2:4][C:7]1([C:20]([O:22][CH3:23])=[O:21])[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 24823OzoneHCID 529878041-tert-Butyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate

Product 1

HCID 589286301-Tert-butyl 4-methyl 4-(2-oxoethyl)piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ozone was bubbled through a −78° C. solution of 1-tert-butyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate (4.0 g, 14.1 mmol) in 3:1 dichloromethane:methanol over 30 min to produce a blue solution. Nitrogen was bubbled through the reaction mixture for 30 min, then dimethylsulfide (5.2 mL, 70.6 mmol) was added and the reaction warmed to room temperature. After 3 h, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 5 to 50% ethyl acetate:hexane to give the title compound (1.72 g). MS: m/z 230.1 (M−tBu).

Workup

  1. customNitrogen was bubbled through the reaction mixture for 30 min
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with a gradient of 5 to 50% ethyl acetate

Sources & evidence

ORD record
ord-449692c04915438385c8a97a73ec1eff
Source dataset
uspto-grants-2010_02
Patent number
US07659264B2

Reaction notes

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