Reaktion #326920

Reaktionsgleichung

2-methylcyclohexylamine

1,3-propane sultone

→

3-[(1R,2S)-2-methylcyclohexyl]amino-1-propanesulfonic acid

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 2 hours
2. 2
   FiltrationThe solid material was collected by filtration
3. 3
   Waschenwashed with acetone (2×50 mL)
4. 4
   workup.DISSOLUTIONThe solid was dissolved in 50% EtOH/water (200 mL)
5. 5
   workup.ADDITIONand solution was treated with Dowex 50WX8 resin (15 g)
6. 6
   workup.STIRRINGThe suspension stirred at room temperature for 15 min
7. 7
   SonstigeThe resin was removed by filtration
8. 8
   EinengenThe filtrate was concentrated to half of the original volume on a rotary evaporator
9. 9
   SonstigeThe solid product slowly crystallized
10. 10
    FiltrationThe product was collected by filtration
11. 11
    Waschenwashed with acetone (2×50 mL)
12. 12
    Sonstigedried in a vacuum oven (50° C.)
13. 13
    Sonstigeto afford compound DJ (10.4 g, 53%)

Vorschrift

To a solution of 2-methylcyclohexylamine (98% cis and trans isomers, 10.0 g, 88.3 mmol) in tetrahydrofuran (60 mL) was slowly added a solution of 1,3-propane sultone (10.5 g, 84.1 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 acetone (2×50 mL). The solid was dissolved in 50% EtOH/water (200 mL); and solution was treated with Dowex 50WX8 resin (15 g). The suspension stirred at room temperature for 15 min. The resin was removed by filtration. The filtrate was concentrated to half of the original volume on a rotary evaporator. The solid product slowly crystallized. The product was collected by filtration, washed with acetone (2×50 mL) and dried in a vacuum oven (50° C.), to afford compound DJ (10.4 g, 53%): 1H NMR (D2O, 500 MHz) δ ppm 3.15 (m, 1H), 3.03 (m, 1H), 2.88 (t, 2H, J=7.3 Hz), 2.76 (m, 1H), 1.98 (m, 3H), 1.68 (m, 2H), 1.51 (m, 2H), 1.18 (m, 3H), 1.01 (m, 1H), 0.92 (m, 3H). 13C NMR (D2O, 125 MHz) δ ppm 62.97, 48.16, 42.72, 34.77, 33.50, 27.57, 24.51, 24.23, 21.51, 17.80. ES-MS 234 (M−1).

Quelle