Propane sultone → 1-Propanesulfonic acid, 3-[(2,3-dimethylcyclohexyl)amino]-

To a solution of 2,3-dimethylcyclohexylamine (10.0 g, 79.0 mmol) in tetrahydrofuran (60 mL) was slowly added a solution of 1,3-propane sultone (9.3 g, 75.0 mmol) in THF (20 mL). The solution was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with THF (50 mL) and acetone (50 mL). The solid was dissolved in 25% EtOH/water (150 mL), and treated with Dowex 50WX8 resin (15 g). The suspension stirred at room temperature for 5 minutes. The resin was removed by filtration. The filtrate was concentrated to dryness under reduced pressure; and the solid residue was suspended in acetone (100 mL). The solid material was collected by filtration, and dried in vacuo; affording compound DK (7.4 g, 43%). 1H NMR (D2O, 500 MHz) 8 ppm 3.29 (m, 0.5H), 3.09 (m, 2H), 2.88 (t, 2H, J=7.3 Hz), 2.80 (m, 0.5H), 1.99 (m, 3H), 1.40 (m, 7H), 0.81 (m, 6H). 13C NMR (D2O, 125 MHz) 8 ppm 62.85, 61.56, 59.88, 58.22, 48.26, 48.15, 44.29, 43.84, 43.59, 42.65, 42.01, 41.03, 37.34, 36.12, 34.73, 34.45, 33.88, 33.64, 29.39, 28.00, 26.50, 24.25, 24.02, 23.64, 22.42, 21.55, 21.45, 21.35, 19.38, 19.13, 18.82, 18.40, 14.38, 13.39, 4.59. ES-MS 248 (M−1).

1. temperatureat reflux for 2 hours
2. filtrationThe solid was collected by filtration
3. washwashed with THF (50 mL) and acetone (50 mL)
4. dissolutionThe solid was dissolved in 25% EtOH/water (150 mL)
5. additiontreated with Dowex 50WX8 resin (15 g)
6. stirringThe suspension stirred at room temperature for 5 minutes
7. customThe resin was removed by filtration
8. concentrationThe filtrate was concentrated to dryness under reduced pressure
9. filtrationThe solid material was collected by filtration
10. customdried in vacuo

ORD-Eintrag

ord-6cf2ac762d7c4fc3ab0e7704b415a66d

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08642801B2