Sodium borohydride → (4-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-yl)methanol

HRID 595928Notes

Reaction equation

HRID 595928 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([CH:14]=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([CH2:14][OH:15])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1180452994-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-carbaldehyde

Product 1

HCID 118045465(4-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-yl)methanolYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice cooled solution of 4-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-carbaldehyde (560 mg, 2.68 mmol) in methanol (18 mL) was added sodium borohydride (91 mg, 2.41 mmol). The reaction solution was stirred at ambient temperature for 30 min. The solvent was removed under vacuum. The residue was diluted with ethyl acetate, and was washed with water, brine, dried over sodium sulfate, filtered and concentrated to give (4-(6-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-yl)methanol (550 mg, 2.60 mmol, 97%) as brown color oil. LCMS (m/z): 212 (MH+), 0.42 min.

Workup

  1. customThe solvent was removed under vacuum
  2. additionThe residue was diluted with ethyl acetate
  3. washwas washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9c130c1269a44013ba326dc34fef205b
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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