HCID 14777246, compound → HCID 62878847, compound

HRID 1481215Notes

Reaction equation

HRID 1481215 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH:7]([C:14]#[N:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[C:1]([O:5][C:6](=[O:16])[CH:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:14][NH2:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 14777246HCID 14777246, compound

Product 1

HCID 62878847HCID 62878847, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Cyano-phenyl-acetic acid tert-butyl ester (4.52 g) was mixed with Raney nickel (5 mL, 50% water) in MeOH (100 mL) and stirred under hydrogen balloon at rt overnight. The mixture was then filtered through Celite and concentrated to give crude product (4.36 g). 1H NMR in CDCl3, δ in ppm: 7.4-7.2 (m, 5H), 3.54 (m, 1H), 3.3-2.9 (br, 2H), 1.41 (s, 9H).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f54debf8b40049479d4f640e7794554a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…