Sodium borohydride → HCID 43394335, compound

HRID 1895907Notes

Reaction equation

HRID 1895907 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:23])([F:22])[O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1>C(O)C>[F:23][C:4]([F:3])([F:22])[O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]2[CH2:16][CH2:17][CH:18]([OH:21])[CH2:19][CH2:20]2)(=[O:13])=[O:14])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59565074HCID 59565074, compound

Product 1

HCID 43394335HCID 43394335, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (719 mg, 19.0 mmol) was added in portions to a suspension of 1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-one (3.07 g, 9.50 mmol) in ethanol (50 ml) at 0° C. and stirred at room temperature for 2 hours. The reaction was quenched with acetone (50 ml) at 0° C. and concentrated in vacuo. The residue was diluted with ethyl acetate (100 ml), washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo to give 1-(4-(trifluoromethoxy)phenylsulfonyl)piperidin-4-ol (3.09 g, 100%) as a white solid: LCMS: 326 [M+1]+.

Workup

  1. customThe reaction was quenched with acetone (50 ml) at 0° C.
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate (100 ml)
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6654cbde3cb41839bf38c7ffb9c8b4a
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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