Reaktion #56750

Reaktionsgleichung

water

[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol

brosyl chloride

triethylamine

→

title compound

Ausbeute 76.9%

[(2R)-8-Methyl-2,3-Dihydro[1,4]Dioxino[2,3-f]Quinolin-2-yl]Methyl 4-Bromobenzenesulfonate

Ausbeute 76.9%

Lösungsmittel

isopropyl alcohol

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe two layers were separated
2. 2
   ExtraktionThe organic layer was extracted with 8% NaHCO3 (20 mL) and H2O (20 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe solid obtained
7. 7
   Filtrationthen filtered
8. 8
   Waschenwashed with (5:1) IPA
9. 9
   Trocknentoluene (2×5 mL) and dried in a vacuum oven

Vorschrift

A solution of [(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol (4.0 g, 17.3 mmol), brosyl chloride (4.86 g, 19.0 mmol), dimethylamino pyridine (20 mg, 0.16 mmol) and triethylamine (3.62 mL, 25.8 mmol) in toluene (40 mL) was stirred at 60° C. for 6 h. The reaction mixture was cooled to room temperature then water (20 mL) was added. After 30 min, the two layers were separated. The organic layer was extracted with 8% NaHCO3 (20 mL) and H2O (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The solid obtained was dissolved in isopropyl alcohol (50 mL) and toluene (10 mL) at 80° C., cooled to room temperature over 1 h then filtered, washed with (5:1) IPA: toluene (2×5 mL) and dried in a vacuum oven to give 5.99 g (76.9%) of the title compound as an off-white solid. 13C NMR (CDCl3) δ 157.9, 144.3, 138.1, 134.7, 132.9, 129.7, 129.6, 129.0, 122.4, 121.7, 121.3, 118.8, 70.7, 67.6, 64.5, 25.4

Quelle