HCID 15671289, compound → HCID 14555261, compound

HRID 1681436Notes

Reaction equation

HRID 1681436 reaction equation
[CH3:1][C@@H:2]([NH:9][C:10]([C:12]1[O:13][C:14]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:15]=2[C:16](=[O:18])[CH:17]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[Ni].C(O)C>[CH3:1][C@@H:2]([NH:9][C:10]([CH:12]1[CH2:17][C:16](=[O:18])[C:15]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:14]=2[O:13]1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 15671289HCID 15671289, compound

Product 1

HCID 14555261HCID 14555261, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (100 mg) was added to a solution of (-)-N-[(R)-α-methylbenzyl]-6-fluoro-4-oxo-4H-1-benzopyran-2-carboxamide (1.00 g, 3.21 mmol, obtained in Example 9 or 10) in ethanol (20 ml) and the mixture was hydrogenated for 1 hour at a temperature of 55°-60° C. under H2 atomosphere (1 kg/cm2) with stirring. It was determined that the (+)-isomer/(-)-isomer ratio of the reduction product was 1.4/1 (26% d.e.) by 1H-NMR analysis.

Sources & evidence

ORD record
ord-628171c3a33c49ea91874d742ed24caf
Source dataset
uspto-grants-1992_12
Patent number
US05171865

Reaction notes

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