반응 #10073

반응 방정식

4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione

furan-2-carbaldehyde

Sodium borohydride

→

product

수율 35.4%

2-(2,6-Dioxo(3-piperidyl))-4-[(2-furylmethyl)amino]isoindoline-1,3-dione

수율 35.4%

용매

acetic acid

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for 5 hours
3. 3
   기타The solvent was evaporated in vacuo
4. 4
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (100 ml)
5. 5
   세척washed with H2O (3×100 ml), saturated aqueous NaHCO3 (2×100 ml), brine (1×100 ml)
6. 6
   기타dried
7. 7
   기타The solvent was evaporated
8. 8
   기타the residue was purified by chromatography (ethyl acetate/hexane, 1:1)

실험 절차

To a suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2 mmol) in acetic acid (20 ml) was added furan-2-carbaldehyde (0.20 g, 2.05 mmol). The mixture was heated to reflux for 5 hours and allowed to cool at room temperature. Sodium borohydride (80 mg, 2 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. The solvent was evaporated and the residue was purified by chromatography (ethyl acetate/hexane, 1:1) to give 0.25 g (35%) of product as a yellow solid: mp 171–173° C.; 1H NMR (DMSO-d6) δ 11.10 (s, 1H), 7.58 (t, J=7.1 Hz, 2H), 7.18 (d, J=8.6 Hz, 1H), 7.08–6.97 (m, 2H), 6.39–6.36 (m, 2H), 5.06 (dd, J=5.2 and 12.4 Hz, 1H), 4.57 (d, J=6.0 Hz, 2H), 2.96–2.82 (m, 1H), 2.63–2.46 (m, 2H), 2.06–2.02 (m, 1H; 13C NMR (DMSO-d6) δ 172.76, 170.01, 168.75, 167.21, 151.97, 145.81, 142.42, 136.05, 132.09, 117.60, 111.04, 110.42, 109.73, 107.38, 48.57,30.95,22.10; Anal. Calcd. For C18H15N3O5: C, 61.19; H, 4.28; N, 11.89. Found: C, 61.02; H, 4.24; N, 11.81.

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