Methyl iodide → N-tert-butyl-1-methylcyclopropane-1-sulfonamide

Temperature

-78 °C

A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to −78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to −78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to −78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).

1. customThe dry ice bath was removed
2. temperatureto warm to rt over a period of 1.5 h
3. temperatureThis mixture was then cooled to −78° C.
4. temperatureThe reaction mixture was warmed to rt
5. temperatureto warm to rt overnight
6. customquenched with saturated NH4Cl (100 mL) at rt
7. extractionIt was extracted with EtOAc (100 mL)
8. washThe organic phase was washed with brine (100 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated in vacuo
11. customto give a yellow oil which
12. customwas crystallized from hexane

ORD record

ord-5a6d61a506144cb6ae560b60dce21783

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07173004B2