Methanesulfonyl chloride → 3-Azido-3-methylbutyl methanesulfonate

Participants

Reaction Steps

To a stirred ice cold solution of 3-azido-3-methylbutan-1-ol (3.33 g, 25.8 mmol) and DIEA (9.0 mL, 2 equiv, 51.6 mmol) in anhydrous DCM (200 mL) was added methanesulfonyl chloride (2.99 mL, 1.5 equiv, 38.7 mmol) over 5 min. The reaction was stirred and left at 0° C. for 1.5 h. The reaction mixture was extracted with 1 N HCl (2×200 mL), saturated NaHCO3 (2×200 mL) and brine (200 mL). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated to give a colorless liquid. The crude oil was purified on an ISCO purification system with gradient elution from 5-40% ethyl acetate in hexanes. The desired fractions were collected and concentrated to give a colorless liquid (4.45 g, 83.4). 1H NMR (CDCl3, 400 MHz): δ 1.36 (s, 6H), 1.93-1.98 (t, J=6.8, 2H), 3.32-4.36 (t, J=6.8, 2H).

Provenance & Evidence