Hydrochloric Acid → cis-3-(1H-pyrazol-1-yl)cyclopentanol

HRID 655149Notes

Reaction equation

HRID 655149 reaction equation
[N:1]1([CH:6]2[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1.[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>CO>[N:1]1([C@@H:6]2[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 594861173-(1H-pyrazol-1-yl)cyclopentan-1-one

Product 1

HCID 67133889cis-3-(1H-pyrazol-1-yl)cyclopentanolYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(1H-pyrazol-1-yl)cyclopentan-1-one (14.09 g, 93.8 mmol) in MeOH (150 ml) was added portionwise NaBH4 (1.77 g. 46.8 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=2/1→1/1) to yield cis-3-(1H-pyrazol-1-yl)cyclopentanol (10.41 g, 73%) as colorless oil.

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=2/1→1/1)

Sources & evidence

ORD record
ord-9db59f582b614807af6455db8a6fef68
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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