Reaktion #155565

Reaktionsgleichung

((2R*,3R*,4S*)-4-Amino-4-(2,4-difluorophenyl)-2-methyltetrahydrofuran-3-yl)methanol

Benzoyl isothiocyanate

→

title compound

Ausbeute 82.8%

N-(((3S*,4R*,5R*)-3-(2,4-Difluorophenyl)-4-(hydroxymethyl)-5-methyltetrahydrofuran-3-yl)carbamothioyl)benzamide

Ausbeute 82.8%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated in vacuo
2. 2
   Sonstigepurified by column chromatography
3. 3
   Wascheneluting with 0-30% EtOAc in n-hexane

Vorschrift

((2R*,3R*,4S*)-4-Amino-4-(2,4-difluorophenyl)-2-methyltetrahydrofuran-3-yl)methanol (120 mg, 0.49 mmol) was dissolved in DCM (2 mL). Benzoyl isothiocyanate (66 μl, 0.49 mmol) was added and the reaction was stirred at room temperature for 30 minutes. The reaction mixture was concentrated in vacuo and purified by column chromatography, eluting with 0-30% EtOAc in n-hexane to leave the title compound as a yellow oil (165 mg). 1H NMR (400 MHz, CDCl3) δ ppm: 11.81 (s, 1H), 8.89 (s, 1H), 7.84-7.91 (m, 2H), 7.62-7.75 (m, 2H), 7.49-7.58 (m, 2H), 6.91 (dt, J=1.71, 8.38 Hz, 1H), 6.80 (ddd, J=2.63, 8.80, 11.80 Hz, 1H), 4.69 (d, J=10.15 Hz, 1H), 4.39 (dd, J=1.71, 10.15 Hz, 1H), 3.91-4.08 (m, 3H), 2.85 (dd, J=4.58, 6.79 Hz, 1H), 2.59 (dt, J=3.73, 8.10 Hz, 1H), 1.37 (d, J=5.99 Hz, 3H).

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