Water → 1-(Pyridin-4-yl)piperidine-4-carboxylic acid

HRID 618168Notes

Reaction equation

HRID 618168 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:17][CH2:16][CH:10]([C:11]([O:13]CC)=[O:12])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Li+].[OH-].O>C1COCC1>[N:1]1[CH:2]=[CH:3][C:4]([N:7]2[CH2:17][CH2:16][CH:10]([C:11]([OH:13])=[O:12])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 9899468Ethyl 1-(pyridin-4-yl)piperidine-4-carboxylate

Product 1

HCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ester 21-1 (10 g, 42.7 mmol) in THF (50 mL) was treated with 1N LiOH (47 mL, 47.0 mmol) and H2O (50 mL). The resulting solution was concentrated and the aqueous residue cooled to 0° C., then adjusted to pH≈6 with 1N HCl and the resulting solid 21-2, collected by filtration.

Workup

  1. concentrationThe resulting solution was concentrated
  2. filtrationthe resulting solid 21-2, collected by filtration

Sources & evidence

ORD record
ord-154c1f0538824074bb19588dd599f2b1
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

Loading…