Methanesulfonyl chloride → (S)-[[(Methylsulfonyl)oxy]methyl]piperidine-1-carboxylic Acid tert-Butyl Ester

HRID 272095Notes

Reaction equation

HRID 272095 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:16][S:17]([O:15][CH2:14][C@H:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1514448tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 10469651(S)-[[(Methylsulfonyl)oxy]methyl]piperidine-1-carboxylic Acid tert-Butyl Ester

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 7.96 g of {(3S)-1-(tert-butoxycarbonyl)-3-piperidyl}methanol in 150 ml of chloroform, 3.4 ml of methanesulfonyl chloride and 6.7 ml of triethylamine were added under cooling with ice, followed by an hour's stirring at room temperature. The reaction liquid was distilled off under reduced pressure, diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution was added, followed by 1.5 hours' stirring. Thereafter the reaction liquid was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate. Distilling the solvent off, 10.50 g of the title compound was obtained.

Workup

  1. temperatureunder cooling with ice
  2. waitfollowed by an hour
  3. customThe reaction liquid
  4. distillationwas distilled off under reduced pressure
  5. additiondiluted with ethyl acetate and saturated aqueous sodium bicarbonate solution
  6. additionwas added
  7. stirring' stirring
  8. customThereafter the reaction liquid
  9. washwas successively washed with water and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationDistilling the solvent off, 10.50 g of the title compound
  12. customwas obtained

Sources & evidence

ORD record
ord-ca7c0447b0a8472bad456b9a69a843df
Source dataset
uspto-grants-2008_11
Patent number
US07452908B2

Reaction notes

Loading…