Ethyl Acetate → tert-Butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylate

HRID 1801565Notes

Reaction equation

HRID 1801565 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20]>>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[CH2:20][C:19]([O:22][CH2:23][CH3:24])=[O:21])[CH2:12][CH2:13]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

HCID 6618868tert-Butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-1-carboxylateYield 52.1%

Procedure

To a mixture of ethyl N-Boc-piperidine-4-carboxylate (0.5 mol) and ethyl acetate (3 mol) t-BuOK (1.5 mol) was added in some portions at 0 C. The mixture was stirred at room temperature for 3 h (monitored by TLC), concentrated up to a half of volume, diluted with water (200 mL) and extracted with ether. Organic layer was dried over sodium sulfate and evaporated in vacuo. Purification by column chromatography (silica gel, ethyl acetate/hexane) afforded 4-(2-ethoxycarbonyl-acetyl)-piperidine-1-carboxylic acid tert-butyl ester (78 g, 52%)

Workup

  1. additionwas added in some portions at 0 C
  2. concentrationconcentrated up to a half of volume
  3. additiondiluted with water (200 mL)
  4. extractionextracted with ether
  5. dry with materialOrganic layer was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customPurification by column chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-61598da507cf4a8e9b414b914f5dbfec
Source dataset
uspto-grants-2013_01
Patent number
US08349833B2

Reaction notes

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