Lithium hydroxide, monohydrate → 6-(1-(Tert-butoxycarbonyl)piperidin-4-yl)picolinic acid

HRID 1910980Notes

Reaction equation

HRID 1910980 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:19]=[C:18]([C:20]([O:22]CC)=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66686619Ethyl 6-[1-(tert-butoxycarbonyl)piperidin-4-yl]pyridine-2-carboxylate

Product 1

HCID 666866476-(1-(Tert-butoxycarbonyl)piperidin-4-yl)picolinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-[1-(tert-butoxycarbonyl)piperidin-4-yl]pyridine-2-carboxylate (500 mg) in tetrahydrofuran (5 ml) and water (1.3 ml) is added, at room temperature, lithium hydroxide monohydrate (125 mg). The mixture is stirred at room temperature for 2 h and then admixed with ice-cold 1N HCl solution. The aqueous phase is extracted with ethyl acetate and then the combined organic phases are dried over sodium sulphate. The solids are filtered off and the solvent is distilled off. This gives 6-[1-(tert-butoxycarbonyl)piperidin-4-yl]pyridine-2-carboxylic acid (310 mg).

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. dry with materialthe combined organic phases are dried over sodium sulphate
  3. filtrationThe solids are filtered off
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-bd7df2a6b8444230a0d809765594de09
Source dataset
uspto-grants-2013_12
Patent number
US08604040B2

Reaction notes

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