반응 #10087

반응 방정식

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

pentanal

acetic acid

sodium triactoxyborohydride

→

product

수율 21.3%

3-[1-Oxo-4-(pentylamino)isoindolin-2-yl]piperidine-2,6-dione

수율 21.3%

용매

ethyl acetate

DMF

반응 조건

후처리

1. 1
   기타The solvent was evaporated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (100 ml)
3. 3
   세척washed with H2O (3×100 ml), brine (1×100 ml)
4. 4
   건조dried over MgSO4
5. 5
   기타The solvent was evaporated
6. 6
   기타the residue was partially purified by chromatography (ethyl acetate/hexane, 75:25)
7. 7
   기타to give an off-white solid which
8. 8
   여과filtered

실험 절차

To a stirred solution of 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione (0.52 g, 2.0 mmol) in DMF (10 ml) was added pentanal (0.26 g, 3.0 mmol), acetic acid (0.24 g, 4.0 mmol), and sodium triactoxyborohydride (0.85 g, 4.0 mmol). The reaction mixture was stirred at room temperature for 6 hours. The solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate (100 ml), washed with H2O (3×100 ml), brine (1×100 ml), and dried over MgSO4. The solvent was evaporated and the residue was partially purified by chromatography (ethyl acetate/hexane, 75:25) to give an off-white solid which was slurried in ethyl acetate and filtered to give 0.14 g (21%) of product as a white solid: mp 244–246° C.; 1H NMR (DMSO-d6) δ 11.00 (s, 1H), 7.28 (t, J=7.7 Hz, 1H), 6.92 (d, J=7.3 Hz, 1H), 6.73 (d, J=8.0 Hz, 1H), 5.54 (t, J=5.3 Hz, 1H), 5.12 (dd, J=5.1 and 13.2 Hz, 1H), 4.24 (d, J=17.2 Hz, 1H), 4.13 (d, J=17.2 Hz, 1H) 3.15–3.07 (m, 2H), 3.00–2.86 (m, 1H), 2.65–2.59 (m, 1H), 2.39–2.23 (m, 1H), 2.08–1.99 (m, 1H), 1.61–1.57 (m, 2H), 1.41–1.32 (m, 4H), 0.89 (t, J=6.8 Hz, 3H); 13C NMR (DMSO-d6) δ 172.83, 171.19, 168.86, 143.74, 132.00, 129.15, 126.42, 111.66, 109.86, 51.46, 45.69, 42.68, 31.20, 28.80, 28.21, 22.79, 21.96, 13.89; Anal. Calcd. For C18H23N3O3: C, 65.63; H, 7.04; N, 12.76. Found: C, 65.69; H, 7.22; N, 12.55.

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