Hydrochloric Acid → 6-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)pyridine-3-carboxylic acid

HRID 1427048Notes

Reaction equation

HRID 1427048 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][N:17]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>C(O)C>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][CH:13]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][N:17]=2)[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86730350Methyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)nicotinate

Product 1

HCID 867303496-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)pyridine-3-carboxylic acidYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2 M sodium hydroxide solution (20 mL) was added to a solution of methyl 6-(1-(tert-butoxycarbonyl)piperidin-4-yl)nicotinate described in Production Example 28-2 (1.07 g, 3.32 mmol) in ethanol (5 mL), and the mixture was stirred for 1 hour. 2 M hydrochloric acid was added to the reaction liquid at 0° C. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum to obtain the title compound (534 mg, 52%).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layer was washed with a saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe drying agent was separated by filtration
  5. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4f2dfd6fb92c4eea90ae5c4f177f9485
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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