N-Fluorobenzenesulfonimide → HCID 11516742, compound

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Reaction Steps

To a 250 ml round bottom flask equipped with condenser was added 3.2 g (7.2 mmol) of the product from Example 9, 3.5 g (10.8 mmol) of N-fluorobenzenesulfonimide and 100 ml of acetonitrile. The solution was heated to reflux for 4 hours. At the end of this time the solution was concentrated and the residue washed with saturated potassium carbonate solution and extracted with ethyl acetate (3×50 ml). The organic layers were combined dried (MgSO4) and concentrated and the resulting crude material chromatographed with 20% ethyl acetate:hexane to yield 1.5 g of material. The enantiomers can be separated (see below) or this material can be hydrolyzed by dissolving in 50 ml of MeOH and 2 ml of 2N NaOH added. After 0.5 hr the solution was concentrated and neutralized with 2N HCL then extracted with ethyl acetate (3×50 ml). The organic layers were combined dried (MgSO4) and concentrated and the solid once again chromatographed with 40% ethyl acetate:hexane. The solid so obtained was recrystallized from ethyl acetate:hexane to yield 0.45 g of product, mp 184-186° C.

Provenance & Evidence