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 room temperature over a period of 1.5 hours. 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 room temperature, recooled to −78° C. over a period of 2 hours and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to room temperature overnight, quenched with saturated NH4Cl (100 mL) at room temperature. It was extracted with ethyl acetate (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to give a yellow oil which was crystallized from hexane to provide 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 (br s, 1H).

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

ORD record

ord-b854b80a7f2f402d8ed211171e8b9b43

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601686B2