Water → HCID 86692469, compound

HRID 1748520Notes

Reaction equation

HRID 1748520 reaction equation
[OH-].[Na+].O.C([O:6][C:7]([C:9]1([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][N:20]=2)[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:11][CH2:10]1)=[O:8])C>CO.O1CCCC1>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([C:9]2([C:7]([OH:8])=[O:6])[CH2:10][CH2:11][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:17][CH2:18]2)=[N:20][CH:21]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86692455HCID 86692455, compound

Product 1

HCID 86692469HCID 86692469, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4N Aqueous solution of sodium hydroxide (5 ml) and water (5 ml) were added to a solution of 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester (1.0 g) described in Reference Example 81(2) in methanol (10 ml) and tetrahydrofuran (10 ml), and stirred at 80° C. for eight hours. After completion of the reaction, the organic solvent was evaporated and the aqueous layer was washed with diethyl ether. Concentrated hydrochloric acid was added to the aqueous layer under ice cooling, pH was adjusted to 4-5, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid (864 mg) as a colorless solid.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated
  3. washthe aqueous layer was washed with diethyl ether
  4. additionConcentrated hydrochloric acid was added to the aqueous layer under ice cooling
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5beaceb1fe304717b0f6fe8f314aa667
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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