Triethylamine → (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-butyric acid methyl ester

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Reaction Steps

A solution of 2.48 g (10.00 mmol) of methyl (S)-4-(tert-butyldimethylsilyloxy)-2-hydroxybutanoate (J. Am. Chem. Soc. 2005, 127, 1090) in 50 ml of dichloromethane was treated with 2.09 ml (15.00 mmol, 1.5 eq) of triethylamine and at 0° C. during 5 min with 0.82 ml (10.50 mmol, 1.051 eq) of methanesulfonyl chloride. After 1 h at 0° C. the reaction was partitioned between 10% aq. potassium dihydrogenphosphate solution/diethyl ether (×3), the organic phases were washed with sat. aq. sodium hydrogencarbonate solution (freshly prepared) and 10% aq. sodium chloride solution, dried over Na2SO4 and evaporated to give 2.91 g (89%) of the title compound as yellow oil. MS: 327.1 (MH+).

Provenance & Evidence