Methanesulfonyl chloride → 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-benzhydrylazetidin-3-ol (15.0 g) in pyridine (100 ml) was cooled down to −20° C. under a nitrogen atmosphere, and methanesulfonyl chloride (6.33 ml) was added dropwise. The reaction mixture was stirred under a nitrogen atmosphere at −20° C. for 1 hour, then in a water bath for 2.5 days. The reaction mixture was partitioned after addition of water and ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure. Ethanol (10 ml) and hexane (50 ml) was added to the residue, and the precipitated crystals were suspended. The crystals were collected by filtration and washed with hexane. This was dried under aeration at room temperature to give the title compound (5.943 g, 44.8%) as pale yellow crystals. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluent; heptane:ethyl acetate=2:1, 1:1, heptane:ethyl acetate:methanol=50:50:1. 40:60:1, then ethyl acetate:methanol=100:1). The fractions containing the target compound were concentrated to give the title compound (1.58 g, 11.9%) as pale yellow crystals.

Provenance & Evidence