Iodoethane → 1-tert-Butyl 3-methyl 3-ethyl-4-oxopiperidine-1,3-dicarboxylate

HRID 1815817Notes

Reaction equation

HRID 1815817 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][C:20](C)([O-])C.[K+].ICC>C(O)(C)(C)C.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH2:19][CH3:20])([C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 179057301-tert-Butyl 3-methyl 3-ethyl-4-oxopiperidine-1,3-dicarboxylateYield 99.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 26 gm (101 mMol) methyl 1-tert-butoxycarbonyl-4-oxo-3-piperidinecarboxylate and 11.9 gm (106 mMol) potassium tert-butoxide in 300 mL tert-butanol was heated to 70° C. under nitrogen. To this solution were then added 23.6 gm (152 mMol) iodoethane over 20 minutes, and the reaction mixture was heated at reflux for about 16 hours. The reaction mixture was then cooled to room temperature and was diluted with diethyl ether. The organics were washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to provide 28.7 gm (99%) of the desired compound as a yellow oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for about 16 hours
  3. washThe organics were washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-edb5a8eabf2946ea8f6f56c33091e00c
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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