Pyridine → HCID 70589628, compound

Participants

Reaction Steps

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.

Provenance & Evidence