Sodium borohydride → HCID 14373286, compound

HRID 414559Notes

Reaction equation

O[C:2]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+].[H][H]>FC(F)(F)C(O)=O>[C:3]1([CH:2]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 240 mg of 6-[1-hydroxy-1-phenyl(3-pyridyl)methyl]-3,4-dihydrocarbostyril in 5 ml of trifluoroacetic acid at 0° C. was added 280 mg of sodium borohydride. When hydrogen evolution ceased the mixture was stirred at 25° C. for 30 minutes, then the solvent was removed under reduced pressure. The residue was added to aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent removed under reduced pressure and the residue chromatographed on silica gel, eluting with 3% methanol in methylene chloride to give 6-[phenyl(3-pyridyl)methyl]-3,4-dihydrocarbostyril, m.p. 95°-96° C.

Workup

customthe solvent was removed under reduced pressure
additionThe residue was added to aqueous potassium carbonate solution
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent removed under reduced pressure
customthe residue chromatographed on silica gel
washeluting with 3% methanol in methylene chloride

Sources & evidence

ORD record: ord-8836d1fcc9ba400ba06586397e462cdd
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04792561

Reaction notes

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