Sodium borohydride → HCID 64515792, compound

HRID 1508543Notes

Reaction equation

HRID 1508543 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 140909103-(4-Methoxyphenyl)cyclopentan-1-one

Product 1

HCID 64515792HCID 64515792, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a RT solution of 3-(4-methoxyphenyl)cyclopentanone (Step B) (482.5 mg, 2.54 mmol) in MeOH (5 ml) was added sodium borohydride (96 mg, 2.54 mmol). The reaction mixture was stirred under nitrogen for 30 minutes, then, concentrated, added water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure to afford the title compound as a mixture of diastereomers that was used without further purification. Mass spectrum (ESI) 175.3 (M+1 minus 18).

Workup

  1. concentrationconcentrated
  2. additionadded water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-59762882a45a47dba9bb864048a8fad0
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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