Propane sultone → 1-Propanesulfonic acid, 3-[(4-methylcyclohexyl)amino]-

To a solution of 4-methylcyclohexylamine (97% cis and trans isomers, 11.0 g, 97.4 mmol) in tetrahydrofuran (70 mL) was slowly added a solution of 1,3-propane sultone (11.5 g, 92.8 mmol) in THF (20 mL). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, washed with THF (50 mL) and acetone (50 mL). The solid was suspended EtOH. The suspension was stirred at room temperature for 5 minutes. The solid product was collected by filtration, washed with EtOH (50 mL), and dried in a vacuum oven (50° C.), to afford compound DR (16.1 g, 75%). 1H NMR (D2O, 500 MHz) δ ppm 3.08 (m, 2.5H), 2.93 (m, 0.5H), 2.87 (m, 2H), 1.99 (m, 4H), 1.64 (m, 3H), 1.47 (m, 1H), 1.24 (m, 2H), 0.88 (m, 1H), 0.78 (m, 3H). 13C NMR (D2O, 125 MHz) δ ppm 57.35, 56.52, 48.16, 18.05, 43.73, 43.30, 32.45, 31.13, 28.92, 28.69, 27.77, 24.55, 21.65, 21.53, 21.20, 18.38. ES-MS 236 (M+1).

1. temperatureat reflux for 2 hours
2. filtrationThe solid material was collected by filtration
3. washwashed with THF (50 mL) and acetone (50 mL)
4. stirringThe suspension was stirred at room temperature for 5 minutes
5. filtrationThe solid product was collected by filtration
6. washwashed with EtOH (50 mL)
7. customdried in a vacuum oven (50° C.)
8. customto afford compound DR (16.1 g, 75%)

ORD record

ord-c88e6ac6725540f4943b8a78cab44b90

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642801B2