Propane sultone → 3-(cyclopropylamino)propane-1-sulfonic Acid

Temperature

40 °C

To a solution of 1,3-propane sultone (2.246 g, 18.39 mmol) in THF (20.0 mL) was added cyclopropanamine (1.214 mL, 17.51 mmol) at room temperature. Upon completion of addition, the reaction mixture was stirred at 40° C. for 30 min, at which point the mixture became a thick white paste. At the conclusion of this period, the reaction mixture was vigorously stirred at 65° C. for 2 h. After cooling to room temperature, the resulting solid was collected by filtration to afford the tilted compound (0.522 g, 17% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.67 (br. s, 1H), 3.12 (t, J=6.9 Hz, 2H), 2.72-2.63 (m, 1H), 2.60 (t, J=6.8 Hz, 2H), 2.51-2.46 (m, 1H), 1.97-1.85 (m, 2H), 0.79-0.70 (m, 4H).

1. additionUpon completion of addition
2. stirringAt the conclusion of this period, the reaction mixture was vigorously stirred at 65° C. for 2 h
3. temperatureAfter cooling to room temperature
4. filtrationthe resulting solid was collected by filtration

ORD record

ord-c9aa8f09952e421f9572d2bf07c16cb6

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062028B2