Sodium borohydride → 1-(4-Hydroxy-4-[4-fluorophenyl]butyl)-3-(3-hydroxyphenyl)piperidine

HRID 1981543Notes

Reaction equation

HRID 1981543 reaction equation
[O:1]=[C:2]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:7]1.[BH4-].[Na+]>CO>[OH:1][CH:2]([C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 136049101-(4-Oxo-4-[4-fluorophenyl]butyl)-3-(3-hydroxyphenyl)piperidine

Product 1

HCID 137468221-(4-Hydroxy-4-[4-fluorophenyl]butyl)-3-(3-hydroxyphenyl)piperidineYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 230 mg (5 mmole) of 1-(4-oxo-4-[4-fluorophenyl]butyl)-3-(3-hydroxyphenyl)piperidine and 193 mg (5 mmole) of sodium borohydride in 20 ml of methanol was stirred at room temperature overnight. The solvent was removed by evaporation in vacuo, and the residue was partitioned between ethyl acetate and water. The layers were separated, the aqueous phase was further extracted with ethyl acetate, and all the ethyl acetate phases were combined. The resulting ethyl acetate solution was washed with water, followed by saturated sodium chloride, and then it was dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on 150 ml of silica gel, eluting with chloroform/methanol (9:1). The product-containing fractions were combined and evaporated in vacuo to give 125 mg (67% yield) of the title compound as a foam, containing chloroform of solvation.

Workup

  1. customThe solvent was removed by evaporation in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. extractionthe aqueous phase was further extracted with ethyl acetate
  5. washThe resulting ethyl acetate solution was washed with water
  6. dry with materialit was dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on 150 ml of silica gel
  9. washeluting with chloroform/methanol (9:1)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-ec08180c0a0445a49e0ddd46f0b4f852
Source dataset
uspto-grants-1986_06
Patent number
US04593037

Reaction notes

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