Reaktion #10316

Reaktionsgleichung

alcohol

1-(2,4-difluorophenyl)-2-(3-{[(4-fluorophenyl)sulfonyl]methyl}azetidin-1-yl)ethanol

(Diethylamino)sulfur trifluoride

→

title compound

Ausbeute 50.1%

1-[2-(2,4-Difluorophenyl)-2-fluoroethyl]-3-{[(4-fluorophenyl)sulfonyl]methyl}azetidine

Ausbeute 50.1%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise and after 30 minutes the cooling bath
2. 2
   Sonstigewas removed
3. 3
   Sonstigethe reaction was quenched with saturated aqueous sodium hydrogencarbonate solution
4. 4
   Extraktionextracted with dichloromethane
5. 5
   WaschenThe combined organic layers were washed with water and brine
6. 6
   Trocknendried over MgSO4
7. 7
   Sonstigeevaporated in vacuo
8. 8
   SonstigeThe residue was purified by preparative TLC (50% ethyl acetate/isohexane)

Vorschrift

A stirred suspension of the alcohol from Step 1 (130 mg, 0.33 mmol) in dichloromethane (4 mL) under nitrogen was cooled to −10° C. (Diethylamino)sulfur trifluoride (54 μL, 0.41 mmol) was added dropwise and after 30 minutes the cooling bath was removed. After a further 15 minutes, the reaction was quenched with saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by preparative TLC (50% ethyl acetate/isohexane) to give the title compound (64 mg, 50%). 1H NMR (500 MHz, CDCl3) δ 7.91–7.89 (2H, m), 7.40–7.34 (1H, m), 7.27–7.23 (2H, m), 6.90 (1H, t, J=8.2 Hz), 6.79 (1H, t, J=9.5 Hz), 5.70–5.58 (1H, m), 3.49 (2H, q, J=7.4 Hz), 3.38–3.36 (2H, m), 2.95 (2H, q, J=6.7 Hz), 2.90–2.70 (3H, m); m/z (ES+) 388 (M+H)+.

Quelle