Triethylamine → 3-Methylsulfonylamino-1-methylsulfonyloxypropane

HRID 5471

Reaction equation

HRID 5471 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>ClCCl>[CH3:13][S:14]([NH:1][CH2:2][CH2:3][CH2:4][O:5][S:14]([CH3:13])(=[O:16])=[O:15])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 233629523-Methylsulfonylamino-1-methylsulfonyloxypropaneYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-1-propanol (11.47 ml, 150 mmoles) and triethylamine (46 ml, 330 mmoles) in dichloromethane (250 ml) was added methylsulfonyl chloride (25.5 ml, 330 mmoles) with stirring under ice-cooling and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed in turn with an aqueous sodium bicarbnonate and water and dried. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 24.22 g of the desired product (69.8%, white crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed in turn with an aqueous sodium bicarbnonate and water
  4. customdried
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-e88abdf757ee41b9b51549e401c0a380
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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