HCID 69053669, compound → HCID 69058444, compound

HRID 1727195Notes

Reaction equation

HRID 1727195 reaction equation
[C:1]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)([CH3:10])[CH2:4][CH2:5][C:6](OC)=[O:7])#[N:2]>C(O)C.[Ni]>[CH3:10][C:3]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:1][NH:2][C:6](=[O:7])[CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 69053669HCID 69053669, compound

Product 1

HCID 69058444HCID 69058444, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To methyl 4-cyano-4-(2-pyridinyl)pentanoate (Preparation 42, 2.5 g, 11.4 mmol) in ethanol (30 ml) was added Raney nickel (3 g) and the reaction mixture was hydrogenated for 78 h. The reaction mixture was filtered through Celite® washing with ethanol (3.20 ml). The combined organic extracts were concentrated in vacuo to give the crude desired product (2.2 g) which was purified by flash chromatography eluting with dichloromethane:methanol (96:7) to give the pure product as an oil (1.1 g, 5.1%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwashing with ethanol (3.20 ml)
  3. concentrationThe combined organic extracts were concentrated in vacuo
  4. customto give the crude desired product (2.2 g) which
  5. customwas purified by flash chromatography
  6. washeluting with dichloromethane:methanol (96:7)

Sources & evidence

ORD record
ord-91f800353017460aac62d3a4fddcec66
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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