4-Toluenesulfonyl chloride → [(4R,6S)-2,2-dimethyl-6-(toluene-4-sulfonyloxymethyl)-[1,3]dioxan-4-yl]-acetic acid t-butyl ester

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Reaction Steps

To a stirred solution of ((4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-acetic acid t-butyl ester (2.24 g, 7.73 mmol), N,N-diisopropylethylamine (2.00 g, 15.46 mmol), 4-dimethylaminopyridine (0.95 g, 7.3 mmol) in dichloromethane (50 mL) was added p-toluenesulfonyl chloride (2.23 g, 11.59 mmol) at 23° C. under nitrogen and stirred for 3 h. The reaction mixture was diluted with dichloromethane and washed with 2N hydrochloric acid, saturated sodium chloride solution and the organic layer separated, dried over magnesium sulfate and concentrated in vacuo which afforded [(4R,6S)-2,2-dimethyl-6-(toluene-4-sulfonyloxymethyl)-[1,3]dioxan-4-yl]-acetic acid t-butyl ester (2.54 g, 80%) as a yellow waxy solid.

Provenance & Evidence