Sodium borohydride → (5-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methanol

HRID 709809Notes

Reaction equation

HRID 709809 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:7][CH:6]([CH2:8][O:9][C:10]2[C:11]([C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=3[F:28])=[N:12][CH:13]=[C:14]([CH:19]=2)[C:15](OC)=[O:16])[CH2:5][CH2:4][O:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:29])[CH2:7][CH:6]([CH2:8][O:9][C:10]2[CH:19]=[C:14]([CH2:15][OH:16])[CH:13]=[N:12][C:11]=2[C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[F:28])[CH2:5][CH2:4][O:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117760026methyl 5-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate

Product 1

HCID 117760252(5-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methanolYield 105.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methoxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate (950 mg) in methanol (20 mL) was added, at 0° C., sodium tetrahydroborate (1.16 g) by small portions, and the mixture was stirred at 60° C. for 4 hr. The solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (930 mg) as a pale-yellow oil.

Workup

  1. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-23b3cf5ebe5b4824943036141b04c608
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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