Ethyl Acrylate → Tert-butyl 1'-(2-ethoxycarbonyl-ethyl)-[4,4']bipiperidinyl-1-carboxylate

HRID 2106499Notes

Reaction equation

HRID 2106499 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CCO>[CH2:6]([O:5][C:1]([CH2:2][CH2:3][N:24]1[CH2:23][CH2:22][CH:21]([CH:18]2[CH2:17][CH2:16][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:20][CH2:19]2)[CH2:26][CH2:25]1)=[O:4])[CH3:7]

Participants

4

Reactant 2

HCID 8821Ethyl Acrylate2×HCID 117475994,4'-Bipiperidine, 1-boc protected

Product 1

HCID 68690102Tert-butyl 1'-(2-ethoxycarbonyl-ethyl)-[4,4']bipiperidinyl-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 mL (40.6 mmol) ethyl acrylate were added to a solution of 10.0 g (37.3 mmol) tert-butyl[4,4′]bipiperidinyl-1-carboxylate in 100 mL EtOH and the reaction mixture was refluxed for 2 h. To complete the reaction a further 1 mL (9.2 mmol) of ethyl acrylate were added, the mixture was refluxed for 1 h and left overnight at RT. The solvent was eliminated i. vac. and the crude product was further reacted without being purified.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. additionwere added
  3. temperaturethe mixture was refluxed for 1 h
  4. customwithout being purified

Sources & evidence

ORD record
ord-b52131bd717e45e48b977d5fe1cc5576
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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