Diethyl Ether → 1-Tert-butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate

HRID 1073089Notes

Reaction equation

HRID 1073089 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][C@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:15]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:14]1.C(OCC)C>C(Cl)Cl>[O:12]=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:15]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:14]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159282601,2-Piperidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) 2-ethyl ester, (2R,4S)-HCID 178418287HCID 178418287, compound

Product 1

HCID 159282621-Tert-butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 1 l. 138 round bottom flask was added 33.6 g (0.16 mol) of pyridinium chlorochromate, 35 g of powdered 4A molecular sieves and 200 ml of methylene chloride. After stirring the mixture at room temperature for sixty minutes, a solution of 21.3 g (0.078 mol) of ethyl cis-4-hydroxy-N-t-butoxycarbonyl-2-piperidinecarboxylate in 50 ml of methylene chloride was added. After stirring the mixture for sixty minutes at room temperature, 700 ml of diethyl ether was added. The mixture was filtered through three-fourths inch of Celite and three-fourths inch of silica gel (230-400 mesh) in a 650 ml medium porosity sintered glass funnel. The solids were washed with 1 1. of diethyl ether and the filtrate was concentrated under vacuum. To the residue was added 200 ml of diethyl ether and the mixture filtered through three-eighths inch of Celite and three-eighths inch of silica gel (230-400 mesh) in a 150 ml medium porosity sintered glass funnel. The solids were washed with 500 ml of diethyl ether and the filtrate was concentrated under vacuum. The residue was purified by high pressure liquid chromatography to provide 14.6 g of ethyl 4-oxo-N-t-butoxycarbonyl-2-piperidinecarboxylate as a colorless oil.

Workup

  1. stirringAfter stirring the mixture for sixty minutes at room temperature
  2. filtrationThe mixture was filtered through three-fourths inch of Celite and three-fourths inch of silica gel (230-400 mesh) in a 650 ml medium porosity sintered glass funnel
  3. washThe solids were washed with 1 1
  4. concentrationof diethyl ether and the filtrate was concentrated under vacuum
  5. additionTo the residue was added 200 ml of diethyl ether
  6. filtrationthe mixture filtered through three-eighths inch of Celite and three-eighths inch of silica gel (230-400 mesh) in a 150 ml medium porosity sintered glass funnel
  7. washThe solids were washed with 500 ml of diethyl ether
  8. concentrationthe filtrate was concentrated under vacuum
  9. customThe residue was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-185a91cd2d5e4e0ca6eb463bb1d0a6b6
Source dataset
uspto-grants-1990_11
Patent number
US04968678

Reaction notes

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