Reaktion #326933

Reaktionsgleichung

(S)-(−)-2-amino-3-methyl-1-butanol

1,3-propane sultone

→

3-[(1S)-1-(hydroxymethyl)-2-methylpropyl]amino-1-propanesulfonic acid

Lösungsmittel

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 3 h
2. 2
   FiltrationThe solid material was collected by filtration
3. 3
   Waschenwashed with acetone (2×25 mL)
4. 4
   workup.STIRRINGThe suspension was stirred
5. 5
   Temperaturat reflux for 30 seconds
6. 6
   FiltrationThe solid product was collected by filtration
7. 7
   Sonstigedried in a vacuum oven (50° C.)
8. 8
   Sonstigeto afford compound EP (2.9 g, 56%)

Vorschrift

To a solution of (S)-(−)-2-amino-3-methyl-1-butanol (2.50 g, 24.2 mmol) in tetrahydrofuran (35 mL) was slowly added 1,3-propane sultone (2.89 g, 23.0 mmol). The mixture was stirred at reflux for 3 h. The reaction mixture was cooled to room temperature. The solid material was collected by filtration, washed with acetone (2×25 mL). The crude product was suspended in 80% acetone/ethanol (75 mL). The suspension was stirred at reflux for 30 seconds. The solid product was collected by filtration, and dried in a vacuum oven (50° C.), to afford compound EP (2.9 g, 56%). 1H NMR (D2O, 500 MHz) δ ppm 3.78 (dd, 1H), 3.62 (dd, 1H), 3.13 (m, 2H), 2.90 (m, 1H), 2.88 (t, 3H), 1.90 (m, 3H), 0.90 (d, 3H), 0.84 (d, 3H). 13C NMR (D2O, 125 MHz) δ ppm 64.74, 57.24, 48.20, 44.44, 26.98, 21.49, 18.53, 17.00. [α]D=+4.1° (c=0.0017 in water), ES-MS 224 (M−1).

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