Ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)acrylate → Ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)propanoate

HRID 1750073Notes

Reaction equation

HRID 1750073 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[N:19]=[C:18]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]([CH:27]=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[Ni]>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[N:19]=[C:18]([NH:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:23])[CH3:24])[C:17]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66632284Ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)acrylate

Product 1

HCID 66631318Ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)propanoateYield 71.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 8 (2.46 g, 5.4 mmol) was hydrogenated under an atmosphere of H2 (40 psi) using Raney Ni (1.59 g, 27.1 mmol) in THF (120 mL). The reaction was filtered to remove the Raney Ni and the filtrate was concentrated to afford ethyl 3-(6-(4-(benzyloxy)butoxy)-2-pivalamidopyridin-3-yl)propanoate (intermediate 9) (1.76 g, 71.5% crude) as an oil.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the Raney Ni
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2aead0dd6e384353b5df1ad653362dd1
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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