Tert-Butylamine → N-tert-Butylcyclopropanesulfonamide

Temperature

-20 °C

To a round-bottom flask equipped with a stir bar was added tert-butylamine (32.9 mL, 313 mmol) and dry THF (330 mL). The solution was cooled to −20° C. and to the stirred solution was added dropwise cyclopropanesulfonyl chloride (14.5 mL, 142 mmol). The solution was allowed to warm to room temperature with stirring for 18 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in DCM, washed with 1N HCl; water; and then brine. The organic solution was dried over MgSO4, filtered, and then concentrated in vacuo. The resulting solid was recrystallized from hexanes:EtOAc (5:1) to afford N-(tert-butyl)cyclopropanesulfonamide as a colorless crystalline solid (20.95 g, 83%). 1H NMR (400 MHz, CDCl3) δ 4.22 (br. s., 1H), 2.47 (tt, J=8.0, 4.9 Hz, 1H), 1.40 (s, 9H), 1.22-1.16 (m, 2H), 1.04-0.97 (m, 2H).

1. customTo a round-bottom flask equipped with a stir bar
2. temperatureto warm to room temperature
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated in vacuo
5. dissolutionThe residue was dissolved in DCM
6. washwashed with 1N HCl
7. dry with materialThe organic solution was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe resulting solid was recrystallized from hexanes:EtOAc (5:1)

ORD record

ord-a29c0742931245059fffdba9715b7812

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957203B2