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

HRID 709803
Notes
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Reaction equation

HRID 709803 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117760190Methyl 5-((5,5-dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate

Product 1

HCID 117760261(5-((5,5-Dimethyltetrahydrofuran-3-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methanolYield 107.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customThe solvent was evaporated under reduced pressure, saturated brine
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes