Methanol → HCID 66747671, compound

HRID 331707Notes

Reaction equation

HRID 331707 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-c7cc2d80816741ae976c3308409b59e1
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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