Hydrazine hydrate (1:1) → (S)-5-(aminomethyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@@H:12]([CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)[O:11][C:10]2=[O:26])[CH:5]=[CH:6][C:7]=1[I:8].O.NN>C(O)C>[NH2:15][CH2:14][C@@H:12]1[O:11][C:10](=[O:26])[N:9]([C:4]2[CH:5]=[CH:6][C:7]([I:8])=[C:2]([F:1])[CH:3]=2)[CH2:13]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of phthalimide 95 (23.3 g, 50.0 mmol) in ethanol (EtOH, 150 mL) was treated with hydrazine monohydrate (12.52 g, 12.1 mL, 250 mmol, 5.0 equiv) at 25° C., and the resulting reaction mixture was warmed to reflux for 2 h. A white precipitate formed as the reaction mixture refluxed. When TLC and HPLC showed that the reaction was complete, the reaction mixture was cooled to room temperature before being quenched with H2O (100 mL). The aqueous solution was then extracted with CH2Cl2 (3×200 mL), and the combined organic extracts were washed with H2O (2×100 mL) and saturated aqueous NaCl (100 mL), dried over MgSO4, and concentrated in vacuo. The residue was further dried in vacuo to afford the desired (5S)-5-aminomethyl-3-(3-fluoro-4-iodo-phenyl)-oxazolidin-2-one (amine 96, 16.0 g, 95.2% yield) as a white powder. This product was directly used in the subsequent reactions without further purification. C10H10FIN2O2, LCMS (EI) m/e 337 (M++H).