Sodium Hydroxide → 4-Fluoro-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid

HRID 2381171Notes

Reaction equation

HRID 2381171 reaction equation
C([O:3][C:4]([C:6]1([F:22])[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[F:22][C:6]1([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 698104704-Fluoro-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 698103204-Fluoro-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acidYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Fluoro-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid ethyl ester (2.08 g) was dissolved in MeOH (70 ml) at RT and under an argon atmosphere and 3M aqueous NaOH (8.42 ml) was added at RT and the mixture was stirred for 12 h at RT. The solvent was evaporated and 3M HCl was slowly added to adjust the pH between 1-2. The mixture was then extracted twice with AcOEt, the organic layers were collected, washed with brine, dried over sodium sulphate and concentrated to give crude 4-fluoro-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid (1.9 g) as a light brown solid which was used in next reaction step without further purification.

Workup

  1. customThe solvent was evaporated
  2. addition3M HCl was slowly added
  3. extractionThe mixture was then extracted twice with AcOEt
  4. customthe organic layers were collected
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-81172ad4d0c34a0c95143ebe5cd70b3b
Source dataset
uspto-grants-2012_09
Patent number
US08258158B2

Reaction notes

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