Water → HCID 178521544, compound

HRID 1748523Notes

Reaction equation

HRID 1748523 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)=[N:8][CH:9]=1.O>C(O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]2)=[N:8][CH:9]=1.[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]2)=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 866924654-(5-Bromopyridin-2-yl)cyclohexanone

Product 2

HCID 178521544HCID 178521544, compoundHCID 178521545HCID 178521545, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (4.58 g) was added under ice cooling to a solution of 4-(5-bromopyridin-2-yl)cyclohexanone (7.9 g) in ethanol (120 ml), and stirred at the same temperature for an hour. After completion of the reaction, water was added under ice cooling, the organic solvent was evaporated and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give trans-4-(5-bromopyridin-2-yl)cyclohexanol (4.94 g) as a white solid, and cis-4-(5-bromopyridin-2-yl)cyclohexanol (1.16 g) as a colorless oil.

Workup

  1. additionwas added under ice cooling
  2. customthe organic solvent was evaporated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a6dceb590c3243769660125af2ee1788
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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