Pyridine → HCID 70589628, compound
Reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10](O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1(C)[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.N1C=CC=C[CH:31]=1>>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([S:25]([C:22]3[C:23]([CH3:31])=[CH:24][CH:19]=[CH:20][CH:21]=3)(=[O:26])=[O:27])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Procedure
To a solution of 2.39 g (1 mmole) of 1-diphenylmethyl-3-hydroxyazetidine [prepared in the manner described in J. C. S. Chem. Commun. 93 (1968) by S. S. Chatterjee and D. J. Triggle] in 30 ml of pyridine is added 3.8 g (2 equivalents) of p-toluenesulfonyl chloride, and the mixture is stirred at room temperature overnight and evaporated under reduced pressure. The residue is alkalified with an aqueous sodium carbonate solution and extracted with benzene. The extract is washed with water, dried over sodium sulfate, and evaporated under reduced pressure. The resulting brown oily residue (4.5 g) is adsorbed on a column of 20 g of silica gel and eluted with benzene. The eluate is crystallized from ether-hexane to yield 2.55 g of 1-diphenylmethyl-3-toluenesulfonylazetidine having mp. 108° to 110° C. as prisms in 64.8% yield, which is recrystallized from ether to yield the pure product having mp. 110° to 112° C.
Workup
- customevaporated under reduced pressure
- extractionextracted with benzene
- washThe extract is washed with water
- dry with materialdried over sodium sulfate
- customevaporated under reduced pressure
- washeluted with benzene
- customThe eluate is crystallized from ether-hexane
Sources & evidence
- ORD record
- ord-e28ed49f32ca4155b485c5ae0d630507
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04200628
Reaction notes
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