Reaktion #10086

Reaktionsgleichung

3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

furan-2-carbaldehyde

Sodium triacetoxyborohydride

→

product

Ausbeute 29.5%

3-{4-[(2-Furylmethyl)amino]-1-oxoisoindolin-2-yl}piperidine-2,6-dione

Ausbeute 29.5%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturto reflux for 4 hours
3. 3
   SonstigeThe solvent was evaporated in vacuo
4. 4
   workup.DISSOLUTIONthe residue was dissolved in acetic acid (20 ml)
5. 5
   SonstigeThe solvent was evaporated in vacuo
6. 6
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (100 ml)
7. 7
   Waschenwashed with H2O (3×100 ml), saturated aqueous NaHCO3 (2×100 ml), brine (1×100 ml)
8. 8
   Trocknendried over MgSO4
9. 9
   SonstigeThe solvent was evaporated in vacuo
10. 10
    Sonstigethe residue was partially purified by chromatography (100% ethyl acetate)
11. 11
    Sonstigeto give an off-white solid which
12. 12
    Sonstigewas recrystallized from ethanol

Vorschrift

To a stirred suspension of 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione (0.52 g, 2.0 mmol) in methanol (50 ml) was added furan-2-carbaldehyde (0.200 g, 2.05 mmol). The mixture was heated to reflux for 4 hours. The solvent was evaporated in vacuo and the residue was dissolved in acetic acid (20 ml). Sodium triacetoxyborohydride (0.450 g, 2.05 mmol) was added to the reaction mixture. The reaction mixture was stirred for 24 hours. The solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate (100 ml), washed with H2O (3×100 ml), saturated aqueous NaHCO3 (2×100 ml), brine (1×100 ml), and dried over MgSO4. The solvent was evaporated in vacuo and the residue was partially purified by chromatography (100% ethyl acetate) to give an off-white solid which was recrystallized from ethanol to give 0.20 g of product as a white solid: mp 248–250° C.; 1H NMR (DMSO-d6) δ 11.02 (s, 1H), 7.57 (s, 1H), 7.27 (t, J=7.6 Hz, 1H), 6.96 (d, J=7.3 Hz, 1H), 6.85 (d, J=8.0 Hz, 1H), 6.36 (d, J=1.2 Hz, 2H), 6.22 (t, J=5.4 Hz, 1H), 5.12 (dd, J=4.9 and 13.1 Hz, 1H), 4.37 (d, J=5.5 Hz, 2H), 4.27 (d, J=17.2 Hz, 1H), 4.14 (d, J=17.2 Hz, 1H) 3.00–2.86 (m, 1H), 2.65–2.59 (m, 1H), 2.37–2.23 (m, 1H), 2.08–1.99 (m, 1H); 13C NMR (DMSO-d6) δ 172.83, 171.16, 168.70, 152.82, 143.06, 142.00, 132.09, 129.02, 126.76, 112.35, 110.63, 110.33, 107.08, 51.50, 45.73, 31.20, 22.75; Anal. Calcd. For C18H17N3O4: C, 63.71; H, 5.05; N, 12.38. Found: C, 63.41; H, 5.03; N, 11.98.

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