Dimethyl Sulfide → 1-Benzyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate

HRID 1469127Notes

Reaction equation

HRID 1469127 reaction equation
[O:1]=[O+][O-].CC(C)=[CH:6][CH2:7][C:8]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:9]1.CSC.C(N(CC)CC)C>C(Cl)Cl>[O:1]=[CH:6][CH2:7][C:8]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:9]1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 24823OzoneHCID 598689181-Benzyl 3-ethyl 3-(3-methylbut-2-en-1-yl)piperidine-1,3-dicarboxylate

Product 1

HCID 598689161-Benzyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ozone was passed through a solution of 1-benzyl 3-ethyl 3-(3-methylbut-2-en-1-yl)piperidine-1,3-dicarboxylate (35.2 g, 0.0979 mol) in methylene chloride (800 mL) at −78° C. until the color of the solution turned blue. The reaction mixture was then flushed with nitrogen until the blue color dissipated. Dimethylsulfide (Aldrich, cat #: 274380) (14 mL, 0.19 mol) and triethylamine (26.5 mL, 0.19 mol) were added and the mixture was stirred at ambient temperature overnight. The volatile solvent were removed under reduced pressure and purified directly by flash chromatography on a silica gel column with 20% ethyl acetate in hexanes to afford the desired product in quantitative yield. LC/MS 334.2 (M+H)+.

Workup

  1. customThe reaction mixture was then flushed with nitrogen until the blue color
  2. customThe volatile solvent were removed under reduced pressure
  3. custompurified directly by flash chromatography on a silica gel column with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-10b5ffa36a8b44a09e07c0ccce50e766
Source dataset
uspto-grants-2015_04
Patent number
US09006260B2

Reaction notes

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