Sodium borohydride → 4-Phenyl-4-piperidinocyclohexanol

HRID 1464238Notes

Reaction equation

HRID 1464238 reaction equation
[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:8][CH2:9][CH:10]([OH:13])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 133067564-Phenyl-4-piperidinocyclohexanone

Product 1

HCID 1621714-Phenyl-4-piperidinocyclohexanolYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The cyclohexanone derivative of Example 3 (1 g; 3.9 mmole) was dissolved in 50 ml of methanol inside a three-necked round bottom flask equipped with a condenser. 0.5 g of sodium borohydride was added portionwise to this solution. After addition, the mixture was stirred at room temperature for 2 hours. The methanol was removed under reduced pressure to give a solid residue. The solid residue was extracted with ethyl acetate. The ethyl acetate extracts were combined and washed once with water and dried over anhydrous sodium sulfate. Ethyl acetate was removed to give a solid material. The solid was recrystallized from hexane/ether (1:1; v/v) to give the desired cyclohexanol derivative as a white crystalline solid (0.89 g; 85% yield).

Workup

  1. customequipped with a condenser
  2. additionAfter addition
  3. customThe methanol was removed under reduced pressure
  4. customto give a solid residue
  5. extractionThe solid residue was extracted with ethyl acetate
  6. washwashed once with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customEthyl acetate was removed
  9. customto give a solid material
  10. customThe solid was recrystallized from hexane/ether (1:1; v/v)

Sources & evidence

ORD record
ord-588b0926c9a84d7c9f5b6440cebad53f
Source dataset
uspto-grants-1994_04
Patent number
US05304479

Reaction notes

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