Sodium borohydride → 1-(3-(Trifluoromethyl)phenylsulfonyl)piperidin-4-ol

HRID 1895902Notes

Reaction equation

HRID 1895902 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:22])([F:21])[C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1>CO>[F:22][C:4]([F:3])([F:21])[C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:15][CH2:16][CH:17]([OH:20])[CH2:18][CH2:19]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 107098471-(3-(Trifluoromethyl)phenylsulfonyl)piperidin-4-one

Product 1

HCID 37292621-(3-(Trifluoromethyl)phenylsulfonyl)piperidin-4-olYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (180 mg, 4.74 mmol) was added to a solution of 1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-one (2.56 g, 8.34 mmol) in methanol (15 ml) at 0° C., and stirred at room temperature for 1 hour. The reaction was quenched with H2O (50 ml) and extracted with ethyl acetate (20 ml×2). The combined organic phase was washed with H2O (20 ml×2) and brine (20 ml×2), dried over Na2SO4 and concentrated in vacuo to give 1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-ol (2.17 g, 84%) as a white solid: LCMS: 310 [M+1]+.

Workup

  1. customThe reaction was quenched with H2O (50 ml)
  2. extractionextracted with ethyl acetate (20 ml×2)
  3. washThe combined organic phase was washed with H2O (20 ml×2) and brine (20 ml×2)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b6fd2e18d3e54e1c939e1c9fa01842ae
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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