HCID 54314069, compound → HCID 54419805, compound

HRID 1681438Notes

Reaction equation

HRID 1681438 reaction equation
[CH3:1][C@@H:2]([NH:10][C:11]([C:13]1[O:14][C:15]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:16]=2[C:17](=[O:19])[CH:18]=1)=[O:12])[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1>[Ni].C(O)C>[CH3:1][C@@H:2]([NH:10][C:11]([CH:13]1[CH2:18][C:17](=[O:19])[C:16]2[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:15]=2[O:14]1)=[O:12])[C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 54314069HCID 54314069, compound

Product 1

HCID 54419805HCID 54419805, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (400 mg) was added to a solution of (-)-N-[(R)-α-methyl-p-chlorobenzyl]-6-fluoro-4-oxo-4H-1-benzopyran-2-carboxamide (1.00 g, 2.89 mmol, obtained in Example 7) in ethanol (20 ml) and the mixture was hydrogenated for 5 hour at a temperature of 55°-60° C. under H2 atomosphere (4 kg/cm2) with stirring. It was determined that the (+)-isomer/(-)-isomer ratio of the reduction product was 2.7/1 (46% d.e.) by 1H-NMR analysis.

Sources & evidence

ORD record
ord-3e5f81ea58334e82aa137de6560553ef
Source dataset
uspto-grants-1992_12
Patent number
US05171865

Reaction notes

Loading…