1-[2-(2-Methoxy-4-nitrophenoxy)-1,1-dimethylethyl]pyrrolidine → 3-Methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)aniline
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:4]=1[O:5][CH2:6][C:7]([N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:9])[CH3:8]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:18]=[C:17]([CH:16]=[CH:15][C:4]=1[O:5][CH2:6][C:7]([CH3:9])([N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:8])[NH2:19]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
1-[2-(2-Methoxy-4-nitrophenoxy)-1,1-dimethylethyl]pyrrolidine (0.075 g, 0.2551 mmol) was dissolved in EtOAc (10 mL). 10% Pd/C (0.007 g) was added and the reaction hydrogenated under 1 atm of H2. The reaction was stirred for 18 h, filtered through celite and the celite washed with EtOAc (3×30 mL). The combined organics were concentrated to afford 0.063 g (0.2386 mmol, 93%) of the product. 1H NMR (CDCl3) δ 6.80 (d, 1H, J=8.4 Hz), 6.22 (s, 1H), 6.18 (d, 1H, J=8.3 Hz), 3.78 (s, 3H), 3.50 (bs, 2H), 2.68 (bs, 6H), 1.78 (bs, 4H), 1.22 (s, 6H).