Hydrochloric Acid → HCID 178521551, compound

HRID 655159Notes

Reaction equation

HRID 655159 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:2]=1.[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@H:7]2[CH2:8][CH2:9][C@H:10]([OH:13])[CH2:11][CH2:12]2)[CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 200349074-(Pyridin-3-yl)cyclohexan-1-one

Product 1

HCID 178521551HCID 178521551, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3-pyridyl)cyclohexanone (3.22 g, 18.4 mmol) in MeOH (25 ml) was added portionwise NaBH4 (348 mg. 9.30 mmol) at 0° C., and stirred for 30 min at room temperature. The reaction mixture was poured into 0.5M HCl and basified with sat. NaHCO3 aq. and then extracted with CH2Cl2. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Hexane/EtOAc=5/1) to yield trans-4-(3-pyridyl)cyclohexanol (2.48 g, 76%) as a colorless powder.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over anhyd Na2SO4
  3. customfollowed by the removal of solvent
  4. customThe crude product was purified by column chromatography (Hexane/EtOAc=5/1)

Sources & evidence

ORD record
ord-d847363bd1e94293ac0a4310326ab97c
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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