Trifluoroacetic acid → 4-(5-Bromo-3-methylpyridin-2-yl)-4-hydroxycyclohexanone

HRID 1748528Notes

Reaction equation

HRID 1748528 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[C:11]([CH3:26])[C:12]([C:15]2([OH:25])[CH2:24][CH2:23][C:18]3(OCC[O:19]3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1.[OH-].[Na+]>O>[Br:8][C:9]1[CH:10]=[C:11]([CH3:26])[C:12]([C:15]2([OH:25])[CH2:16][CH2:17][C:18](=[O:19])[CH2:23][CH2:24]2)=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 866924748-(5-Bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol

Product 1

HCID 866924774-(5-Bromo-3-methylpyridin-2-yl)-4-hydroxycyclohexanoneYield 41.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Trifluoroacetic acid (11 ml) and water (1 ml) were added to 8-(5-bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol (7.45 g) described in Reference Example 105(1) and stirred at room temperature. After completion of the reaction, water was added and neutralized by the addition of 1N aqueous solution of sodium hydroxide and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxy-cyclohexanone (2.69 g) as a white solid.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5e63ee9959fd4148941415772d062957
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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