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

HRID 1514678Notes

Reaction equation

HRID 1514678 reaction equation
[CH3:1][O:2][C:3](=[O:26])[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])=[CH:21][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:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=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 866462546-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 667181316-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl esterYield 103.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-[3-(4-Fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (2.50 g, 7.02 mmol) and sodium borohydride (553 mg, 14.0 mmol) in methanol (125 mL) were stirred for 2 h at room temperature. Addition of 10% aqueous citric acid (200 mL) and extraction with ethyl acetate yielded 6-[3-(4-fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (2.60 g, quant.) as white solid. MS: m/e=359.2 [M+H]+.

Sources & evidence

ORD record
ord-1a97df060d1f4e478f294ae85865ee7a
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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