4-Fluorobenzenesulfonyl chloride → (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acid

HRID 397663Notes

Reaction equation

HRID 397663 reaction equation
C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=[O:18].C(N(CC)C(C)C)C.[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>[OH-].[Na+].CC(C)=O>[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([OH:19])=[O:18])(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 521913N,N-Diethyl-2-propanamineHCID 69946027(2S)-2-Piperidinecarboxylic acid L-tartrate

Product 1

HCID 768662(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acidYield 96.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

(2S)-2-Piperidinecarboxylic acid L-tartrate (10 g) [see Preparation 1] was dissolved in 1N aqueous sodium hydroxide solution (107.4 ml) and diethylisopropylamine (9.35 ml) was added followed by a solution of 4-fluorobenzenesulphonyl chloride (10.45 g) in acetone (107 ml) at 0° C. The reaction mixture was warmed to room temperature and stirred for 18 hours after which time the solvent was removed under reduced pressure and the residue diluted with 1N aqueous sodium hydroxide solution. The aqueous solution was washed with diethyl ether and acidified with concentrated hydrochloric acid. The product was extracted with ethyl acetate, the organic layers dried over magnesium sulphate and the solvent was removed under reduced pressure to afford (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acid (9.89 g).

Workup

  1. customwas removed under reduced pressure
  2. additionthe residue diluted with 1N aqueous sodium hydroxide solution
  3. washThe aqueous solution was washed with diethyl ether
  4. extractionThe product was extracted with ethyl acetate
  5. dry with materialthe organic layers dried over magnesium sulphate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-870f1d9bb4b247fbb5b6db8f1ee452a0
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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