Methanol → 5-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

HRID 1962987Notes

Reaction equation

HRID 1962987 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[N:16][O:17][C:18]=2/[CH:19]=C/C2C=CC=CC=2)=[CH:8][N:7]=1)=[O:5])[CH3:2].[BH4-].[Na+].C[OH:37]>>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[N:16][O:17][C:18]=2[CH2:19][OH:37])=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 666444395-[3-(4-Fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 666445155-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl esterYield 59%

Procedure

A solution of 5-[3-(4-fluoro-phenyl)-5-((E)-styryl)-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (1.2 g, 3.24 mmol) in methanol (60 mL) was treated at room temperature with sodium borohydride (255.4 mg, 6.48 mmol) and stirred for 1 h. After quenching with aqueous citric acid (100 mL of a 10% solution) and extraction with ethyl acetate the organic phase was dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetete=1:1 to 0:1) afforded the title compound as a white solid (710 mg, 59%). MS: m/e=373.2 [M+H]+.

Workup

  1. customAfter quenching with aqueous citric acid (100 mL of a 10% solution) and
  2. extractionextraction with ethyl acetate the organic phase
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica, heptane:ethyl acetete=1:1 to 0:1)

Sources & evidence

ORD record
ord-dcf3c5d48e014c519bc6d36fa0bd430b
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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