Pyridine → Ethyl 1-(methylsulfonyl)piperidine-4-carboxylate

HRID 1247053Notes

Reaction equation

HRID 1247053 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:18][S:19]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 669104Ethyl 1-(methylsulfonyl)piperidine-4-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl isonipecotate (4.9 mL, 31.8 mmol) and pyridine (2.8 mL, 34.6 mmol) was cooled to 0° C. Methanesulfonyl chloride (2.7 mL, 34.9 mmol) was added. After 1.5 hours, the reaction mixture was diluted with CH2Cl2 (300 mL) and extracted with saturated aqueous NaHCO3 (3×100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The crude material was dissolved in EtOAc (400 mL), extracted with H2O (3×50 mL), dried over Na2SO4, filtered, and concentrated to give the pure product (5.42 g, 22.9 mmol, 72%) as a yellow solid. IR(CHCl3): 3027, 1726, 1331, 1158, 963.

Workup

  1. extractionextracted with saturated aqueous NaHCO3 (3×100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe crude material was dissolved in EtOAc (400 mL)
  6. extractionextracted with H2O (3×50 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b0185a3f2b7d477490ab61948d8b0c7d
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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