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

HRID 1514696Notes

Reaction equation

HRID 1514696 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:28])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:16][O:17][C:18]=2[CH:19]=[O:20])=[N:8][CH:7]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:3][O:4][C:5](=[O:28])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:16][O:17][C:18]=2[CH2:19][OH:20])=[N:8][CH:7]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 866462556-[3-(4-Chloro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 667183126-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (719 mg, 18.2 mmol) was added in portions to 6-[3-(4-chloro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (3.4 g, 9.12 mmol) in methanol (170 mL). After stirring for 1 h at room temperature a solution of citric acid (10% in water) was added. Extraction with ethyl acetate and chromatography (silica, ethyl acetate:heptane=1:9 to 1:1) afforded the title compound (3.11 g, 91%) as a white solid. MS: m/e=375.1 [M+H]+.

Workup

  1. additionwas added
  2. extractionExtraction with ethyl acetate and chromatography (silica, ethyl acetate:heptane=1:9 to 1:1)

Sources & evidence

ORD record
ord-3b2f87155b0d4b75a0ba25580835bc99
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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