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

HRID 1526482Notes

Reaction equation

HRID 1526482 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 extacted 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. dry with materialOrganic layer was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customPurification by column chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fd8778db6bfe4a9c87458c6dd0de9809
Source dataset
uspto-grants-2015_07
Patent number
US09085585B2

Reaction notes

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