Sodium borohydride → (5-((5,5-Dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methanol

HRID 709803Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate (700 mg) in methanol (10 mL) was cooled to 0° C., and sodium tetrahydroborate (342 mg) was slowly added by small portions. The reaction mixture was stirred at 60° C. for 4 hr. The solvent was evaporated under reduced pressure, saturated brine was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (700 mg) as a pale-yellow oil. This compound was used for the next step without further purification.

Workup

customThe solvent was evaporated under reduced pressure, saturated brine
additionwas added to the residue
extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-6ad868598e3947d4952b9a04474df88d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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