Triethylamine → 1-Methanesulfonyl-piperidine-4-carboxylic acid benzyl ester

HRID 589328Notes

Reaction equation

HRID 589328 reaction equation
Cl.[CH2:2]([O:9][C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>CN(C=O)C.O>[CH2:2]([O:9][C:10]([CH:12]1[CH2:17][CH2:16][N:15]([S:26]([CH3:25])(=[O:28])=[O:27])[CH2:14][CH2:13]1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68664822Benzyl piperidine-4-carboxylate hydrochloride

Product 1

HCID 574280631-Methanesulfonyl-piperidine-4-carboxylic acid benzyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Piperidine-4-carboxylic acid benzyl ester, hydrochloride salt (1 g, 3.9 mmol, 1 e.) from step 3, was dissolved in DMF (15 ml), Triethylamine (0.55 ml, 4 mmol, 1 eq.) and methanesulfonylchloride were added. The mixture was stirred for 1 h at room temperature, then was poured in water (20 ml). The aqueous solution was extracted with Ethyl Acetate (90 ml) and the organic layer was dried over anhydrous sodium sulfate, evaporated under reduced pressure to give a colourless oil. Yield 78%, 0.9 g.

Workup

  1. extractionThe aqueous solution was extracted with Ethyl Acetate (90 ml)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure
  4. customto give a colourless oil

Sources & evidence

ORD record
ord-8f728b370b324633a8d2a1bfa4165b1e
Source dataset
uspto-grants-2016_01
Patent number
US09233115B2

Reaction notes

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