Sodium borohydride → cis-3-(2-Pyridyl)cyclopentanol

HRID 655138Notes

Reaction equation

HRID 655138 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8]1.[BH4-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@H:7]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 594861153-(2-Pyridyl)cyclopentan-1-one

Product 1

HCID 67133931cis-3-(2-Pyridyl)cyclopentanolYield 59.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2-pyridyl)cyclopentan-1-one (3.17 g, 19.7 mmol) in MeOH (80 ml) was added portionwise NaBH4 (745 mg. 19.7 mmol) at 0° C., and stirred for 2 h at room temperature. The reaction mixture was poured into ice-water and then extracted with EtOAc. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Hexane/EtOAc=1/1→1/3) to yield cis-3-(2-pyridyl)cyclopentanol (1.90 g, 59%) as colorless oil.

Workup

  1. extractionextracted with EtOAc
  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=1/1→1/3)

Sources & evidence

ORD record
ord-acdc848b83e546ceaaf8cb0f8f32991e
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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