Citric Acid → 6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

HRID 1514708Notes

Reaction equation

HRID 1514708 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:18])=[N:6][CH:5]=1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>CO>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 866462566-[3-(3,4-Difluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 667181646-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl esterYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-[3-(3,4-Difluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (3.50 g, 9.35 mmol) in methanol (125 mL) was treated with sodium borohydride (737 mg, 18.7 mmol) for 30 min at room temperature. Addition of aqueous citric acid solution (10%, 300 mL) and extraction with ethyl acetate afforded the title compound (3.0 g, 85%) as a white solid. MS: m/e=377.2 [M+H]+.

Sources & evidence

ORD record
ord-0e745df3fff447908124d2ea63d2fbb3
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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