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

HRID 1747037Notes

Reaction equation

HRID 1747037 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-d09b01b0b1a8447aa444d584df027dda
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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