Sodium borohydride → cis-3-(3-Pyridyl)cyclohexanol

HRID 655169Notes

Reaction equation

HRID 655169 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[CH:8]=2)[CH:2]=1.[BH4-].[Na+]>CCO.CO.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:12][CH2:11][CH2:10][C@H:9]([OH:13])[CH2:8]2)[CH:2]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 134025713-(Pyridin-3-yl)cyclohex-2-en-1-one

Product 1

HCID 67133573cis-3-(3-Pyridyl)cyclohexanolYield 75%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 3-(3-pyridyl)-2-cyclohexen-1-one (19.1 g, 110 mmol) and 10% Pd/C (1.91 g) in EtOH (300 mL) was stirred under hydrogen atmosphere for 16 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. To a solution of crude product in MeOH (360 ml) was added portionwise NaBH4 (2.08 g. 55.0 mmol) at 3° C., and stirred for 30 min at same temperature. The reaction mixture was poured into ice-water and then extracted with AcOEt. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (NH, Hexane/EtOAc=2/1) to yield cis-3-(3-pyridyl)cyclohexanol (14.6 g, 75%) as colorless oil.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. stirringstirred for 30 min at same temperature
  4. extractionextracted with AcOEt
  5. dry with materialThe organic layer was dried over anhyd Na2SO4
  6. customfollowed by the removal of solvent
  7. customThe crude product was purified by column chromatography (NH, Hexane/EtOAc=2/1)

Sources & evidence

ORD record
ord-9570174edd8d4b2da269d6f4a24bca44
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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