Methanesulfonyl chloride → tert-Butyl [1-(methanesulfonyl)piperidin-4-yl]carbamate

HRID 450760Notes

Reaction equation

HRID 450760 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[C:10]([O:9][C:8](=[O:14])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([S:16]([CH3:15])(=[O:18])=[O:17])[CH2:6][CH2:5]1)([CH3:11])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 25250149tert-Butyl [1-(methanesulfonyl)piperidin-4-yl]carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixed liquid of 1.00 g of tert-butyl piperidin-4-ylcarbamate and 20 ml of pyridine was added 0.77 ml of methanesulfonyl chloride, followed by stirring at room temperature for 18 hours. After evaporating the pyridine under reduced pressure, ethyl acetate was added thereto, followed by washing with a 5% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution. After drying the organic layer over anhydrous magnesium sulfate, the solvent was evaporated, and the obtained solid was washed with diethyl ether to obtain 1.19 g of t-butyl[1-(methylsulfonyl)piperidin-4-yl]carbamate as a white solid.

Workup

  1. customAfter evaporating the pyridine under reduced pressure, ethyl acetate
  2. additionwas added
  3. washby washing with a 5% aqueous citric acid solution
  4. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. washthe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-ee517da78a064bdeab101050b92c80cf
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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