Sodium Bicarbonate → 4-(5-Bromo-3-methylpyridin-2-yl)-4-hydroxycyclohexanone

HRID 1748572Notes

Reaction equation

HRID 1748572 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]([C:8]2([OH:18])[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(=O)([O-])O.[Na+]>Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:19])[C:5]([C:8]2([OH:18])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 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 91.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 8-(5-bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol (23.2 g) described in Reference Example 105 (1) was added 3 N hydrochloric acid aqueous solution (140 ml), and stirred at room temperature for 16 hours. After completion of the reaction, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, the precipitated solid was collected by filtration, and then washed with ethanol to give 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxycyclohexanone (18.3 g) as a pale yellow solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-9cbf2a19e3544c5caf9145d7246d2e43
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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