Methanol → HCID 66747671, compound

HRID 591205Notes

Reaction equation

HRID 591205 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:14]#[N:15])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1.CO.ClCCl>C1COCC1.[Ni]>[CH2:16]([C:5]1([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[CH2:14][NH:15][C:3](=[O:2])[CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 66747345HCID 66747345, compound

Product 1

HCID 66747671HCID 66747671, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyl-3-cyano-3-(3-methoxy-phenyl)-propionic acid methyl ester (200 mg, 0.6 mmol) in THF (20 ml) was added Raney-Nickel (3×300 mg at 0/5/10 h). Hydrogenation occurred at 50° C. over 13 h. Methanol (15 ml) and dichloromethane (15 ml) was added, stirred for 15 min, then the mixture was filtered and the solvent evaporated. The oil was dissolved in dichloromethane, washed with HCl (1M) and brine. The organic layer was dried, filtered and the solvent evaporated. The residue was suspended in pentane, stirred over night, filtered and dried to obtain 153 mg of product.

Workup

  1. filtrationthe mixture was filtered
  2. customthe solvent evaporated
  3. dissolutionThe oil was dissolved in dichloromethane
  4. washwashed with HCl (1M) and brine
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. stirringstirred over night
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-1208ea408b744605a4297f5385533108
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Reaction notes

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