Hydrochloric Acid → (2S)-2-hydroxy-3,3-dimethyl-4-[(methylsulfonyl)oxy]butyl methanesulfonate

Beteiligte Stoffe

Reaktionsschritte

To a 0° C. solution of 25.3 g (189 mmol) of (2S)-3,3-dimethyl-1,2,4butanetriol in 170 mL of pyridine was added dropwise 29.1 mL (378 mmol) of methanesulfonyl chloride. The reaction mixture was allowed to slowly warm to room temperature, stirred for 18 h, and then diluted with dichloromethane. To the mixture was added 200 mL of 1N hydrochloric acid followed by concentrated hydrochloric acid until the pH of the aqueous phase was brought to a value of 2. The mixture was extracted with dichloromethane, and the combined extracts were washed with brine and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10% acetone in dichloromethane to afford 21.75 g (52.10%) of (2S)-2-hydroxy-3,3-dimethyl-4-[(methylsulfonyl)oxy]butyl methanesulfonate. 1H NMR (300 MHz, DMSO-d6) δ 5.48 (d, J=6 Hz, 1H), 4.30 (dd, J=2 Hz, J=10 Hz, 1H), 3.91-4.05 (m, 3H), 3.16 (d, J=4 Hz, 6H), 0.90 (d, J=13 Hz, 6H).

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