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

HRID 403200Notes

Reaction equation

HRID 403200 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-37ffc95b0bb84b32a5d0bd50cd3c6131
Source dataset
uspto-grants-2014_06
Patent number
US08748420B2

Reaction notes

Loading…