Methanesulfonyl chloride → HCID 15296366, compound

HRID 2059918Notes

Reaction equation

HRID 2059918 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([CH2:17][CH2:18][OH:19])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[S:20](Cl)([CH3:23])(=[O:22])=[O:21]>C(Cl)Cl>[CH3:23][S:20]([O:1][CH2:2][CH2:3][C:4]1([CH2:17][CH2:18][O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:6][CH2:5]1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15295828tert-Butyl 4,4-bis(2-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 15296366HCID 15296366, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4,4-bis(2-hydroxyethyl)piperidine-1-carboxylate (500 mg, 1.83 mmol) in DCM (10 ml) were added mesyl chloride (0.33 ml, 4.2 mmol) and TEA (1 ml, 7.32 mmol) at −20° C. and the mixture was stirred for 30 min maintaining the same temperature. TLC revealed completion of the reaction and it was quenched with water and extracted with DCM. The organic phase was washed with brine, dried over Na2SO4 and concentrated to dryness. The crude product was purified by column chromatography (silica (100-200), EtOAc-hexane (30%)) to yield the desired compound. Yield: 70%

Workup

  1. temperaturemaintaining the same temperature
  2. customcompletion of the reaction and it
  3. customwas quenched with water
  4. extractionextracted with DCM
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe crude product was purified by column chromatography (silica (100-200), EtOAc-hexane (30%))

Sources & evidence

ORD record
ord-a3daa622fbee433aa44d978018aa60b0
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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