Methanesulfonyl chloride → HCID 76689234, compound

Participants

Reaction Steps

To a solution of benzyl((4RS,5RS)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methylcarbamate (0.884 g, 2.86 mmol) in dry dichloromethane (30 mL) was added diisopropylethylamine (1.417 ml, 8.57 mmol) and then methanesulfonyl chloride (0.288 ml, 3.71 mmol) and the solution was stirred at RT. After 30 mins the reaction mixture was washed with water, dil HCl and then sat aq NaHCO3. Normal processing afforded a syrup, which was dissolved in DMF (15 mL) and then sodium thiomethoxide (0.601 g, 8.57 mmol) was added with stirring. After 1 h, toluene was added and the mixture was washed with water (×2) and processed normally. Chromatography (EtOAc/Hex 1:2) gave benzyl((4RS,5RS)-2,2-dimethyl-4-(methylthiomethyl)-1,3-dioxan-5-yl)methylcarbamate (0.839 g, 2.472 mmol, 86% yield) as a syrup. 13C NMR (CDCl3) δ 156.9, 136.8, 128.9, 128.6, 128.5, 99.2, 72.3, 67.3, 62.4, 40.4, 39.9, 38.4, 29.0, 20.3, 17.3.

Provenance & Evidence