Triethylamine → N-(3-fluoro-2-methylsulfonyloxypropyl)-N-(2-methylsulfonyloxyethyl)benzylamine
Reaction equation
C(N(CC)CC)C.[CH2:8]([N:15]([CH2:19][CH:20]([OH:23])[CH2:21][F:22])[CH2:16][CH2:17][OH:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[F:22][CH2:21][CH:20]([O:23][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:19][N:15]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:16][CH2:17][O:18][S:25]([CH3:24])(=[O:27])=[O:26]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
7.27 g (0.072 mole) of triethylamine were added to a solution of 6.75 g (0.03 mole) of N-benzyl-N-(3-fluoro-2-hydroxypropyl)ethanolamine [prepared as described in step (a) above] in 200 ml of ethyl acetate. Whilst stirring and ice-cooling the mixture, 8.24 g (0.072 mole) of methanesulfonyl chloride were added to it. After the resulting mixture had been stirred for 3 hours at the same temperature, an aqueous solution of sodium bicarbonate was added to it. The organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 12.49 g of N-(3-fluoro-2-methylsulfonyloxypropyl)-N-(2-methylsulfonyloxyethyl)benzylamine as a pale yellow oil.
Workup
- additionwere added to it
- stirringAfter the resulting mixture had been stirred for 3 hours at the same temperature
- customThe organic layer was separated
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was then removed by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-8bf5566210aa4daa97cb84254b95f558
- Source dataset
- uspto-grants-1996_03
- Patent number
- US05496951
Reaction notes
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