Synthesis
The general procedure for the synthesis of tert-butyl N-methylsulfonylcarbamate from methanesulfonamide and di-tert-butyl dicarbonate was as follows: triethylamine (22.0 mL, 158 mmol), di-tert-butyl dicarbonate (27.5 g, 126 mmol), and 4-(N,N-dimethylamino)pyridine (1.28 g, 10.5 mmol) were sequentially added to a dichloromethane (300 mL) solution of methanesulfonamide (10.0 g, 105 mmol) at 25 °C. amide (10.0 g, 105 mmol) in a solution of dichloromethane (300 mL). The reaction mixture was stirred at 25 °C for 2 h and subsequently concentrated under vacuum to about 40 mL. Ethyl acetate (350 mL) was added to the concentrate and the mixture was washed with 1.0 M aqueous hydrochloric acid (300 mL). The aqueous layer was extracted with ethyl acetate (250 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give tert-butyl N-methylsulfonylcarbamate (17.1 g, 87.6 mmol, 83% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ: 1.53 (9H, s), 3.27 (3H, s).
References
[1] Tetrahedron Letters, 1994, vol. 35, # 3, p. 379 - 380
[2] Patent: US2009/306057, 2009, A1. Location in patent: Page/Page column 44
[3] Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5638 - 5641
[4] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8283 - 8286
[5] Organic Letters, 2006, vol. 8, # 21, p. 4707 - 4710
