Sodium borohydride → 4-bromo-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol

HRID 714061Notes

Reaction equation

HRID 714061 reaction equation
[Br:1][C:2]1[C:3]2[CH2:10][C:9]([CH3:12])([CH3:11])[C:8](=[O:13])[C:4]=2[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]2[CH2:10][C:9]([CH3:11])([CH3:12])[CH:8]([OH:13])[C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 898461634-bromo-6,6-dimethyl-5H-cyclopenta[c]pyridin-7(6H)-one

Product 1

HCID 898459194-bromo-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-6,6-dimethyl-5H-cyclopenta[c]pyridin-7(6H)-one (1.1 g, 4.58 mmol) in MeOH (25 mL) was added NaBH4 (261.3 mg, 6.88 mmol) portion wise. The resulting mixture was stirred for 1 h before it was quenched with water. The solution was concentrated in vacuo and the residue was extracted between EtOAc and H2O (20 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give a crude title product. MS: 243.7 (M+H+, 1 Br).

Workup

  1. customwas quenched with water
  2. concentrationThe solution was concentrated in vacuo
  3. extractionthe residue was extracted between EtOAc and H2O (20 mL×3)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c81731bc1ab4693a8bf8003ee2ec6e6
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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