Triethylamine → 2-(2,3,4,9-Tetrahydrothiopyrano[2,3-b]indol-2-yl)methyl-4,4-dimethyl-2-oxazoline

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Reaction Steps

0.05 ml of methanesulfonyl chloride was added to a mixture of 165 mg of 2-[4-hydroxy-2-(indol-2-ylthio)butyl]-4,4-dimethyl-2-oxazoline (prepared as described in Example 79) and 0.10 ml of triethylamine in 5 ml of dichloromethane, with stirring and ice-cooling, and stirring was continued for 30 minutes. At the end of this time, the reaction mixture was diluted with water and then extracted with ethyl acetate. The ethyl acetate fraction was then washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was dissolved in a mixture of 5 ml of dichloromethane and 5 ml of benzene. 0.26 ml of a solution of 3M ethylmagnesium bromide in diethyl ether was then added to this mixture, with stirring, at room temperature, and stirring was continued at this temperature for 30 minutes. At the end of this time, the reaction mixture was diluted with a saturated aqueous solution of ammonium chloride and then extracted with ethyl acetate. The ethyl acetate fraction was then washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a mixture of 30% v/v ethyl acetate in hexane as the eluent, to afford 73 mg of the title compound as a solid.

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