Methanesulfonyl chloride → 1-Benzhydryl-3-methylazetidin-3-yl methanesulfonate
Reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([CH3:19])([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH:1]([N:14]1[CH2:17][C:16]([O:18][S:21]([CH3:20])(=[O:23])=[O:22])([CH3:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
10 g (0.0394 mol) of 1-benzhydryl-3-methylazetidin-3-ol (S.S. Chattergee and A. Shoeb, Synthesis 1973, p. 153-154) are dissolved in 100 ml of anhydrous pyridine, the mixture is cooled to -20° C. and 7.3 g (0,063 mol) of methanesulphonyl chloride are added dropwise. The temperature is kept below -10° C., stirring is carried out at this temperature for 1 hour and the reaction mixture is left between 0° C. and 3° C. for two days. It is poured into 600 ml of water/ice, the precipitate is recovered by filtration and is washed with water. After drying in the oven at 50° C. for 2 hours the product is taken up in isopropyl ether (100 ml), is filtered and is dried in the oven at 50° C. overnight to obtain approximately 10 g of 1-benzhydryl-3-methanesulphonyloxy-3-methylazetidine.
Workup
- customShoeb, Synthesis 1973, p
- customis kept below -10° C.
- waitthe reaction mixture is left between 0° C. and 3° C. for two days
- filtrationthe precipitate is recovered by filtration
- washis washed with water
- customAfter drying in the oven at 50° C. for 2 hours the product
- filtrationis filtered
- customis dried in the oven at 50° C. overnight
Sources & evidence
- ORD record
- ord-21f5999845684cc6ae3590291b21290d
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576320
Reaction notes
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