反应详情

温度

60 °C

To DMF (10 mL) were added 3β-amino-5-cholestene (Compound 8, 386 mg, 1.0 mmol), N-(3-bromopropyl)phthalimide (295 mg, 1.1 mmol), and K2CO3 (276 mg, 2.0 mmol). The solution was heated to 60° C. and stirred for 24 h. The reaction was cooled to 22° C., and DMF was removed in vacuo. To the resulting residue was added CH2Cl2 (10 mL). The insoluble material was removed by filtration and washed with additional CH2Cl2 (2×5 mL). To the combined filtrate and wash solutions containing the crude secondary amine product was added (Boc)2O (327 mg, 1.5 mmol) and DIEA (0.5 mL, 3.0 mmol). The reaction was stirred for 4 h at 22° C. and concentrated in vacuo. Flash column chromatography (hexanes/ethyl acetate, 8:1) afforded Compound 9 (465 mg, 69%) as a white foam, mp 59-61° C.; 1H NMR (400 MHz, CDCl3) δ 7.83 (m, 2H), 7.69, (m, 2H), 5.30 (d, 1H), 3.68 (t, 2H), 3.13 (br, 3H), 2.01-0.83 (m, 51H), 0.65 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 168.2 (×2), 155.2, 141.3, 133.8 (×2), 132.0 (×2), 123.2 (×2), 79.3, 56.6, 56.1 (×2), 50.1, 42.6 (×2), 39.8, 39.4 (×2), 38.3, 36.8, 36.5, 36.1, 35.9, 35.7, 31.2 (×2), 28.4 (Boc, Me3), 28.2, 27.9, 26.7, 24.2, 23.8 (×2), 22.8, 22.5, 20.9, 19.3, 18.7, 11.8; IR (film) ν max 2935, 2867, 1772, 1715, 1689, 1467, 1395, 1365, 1238, 1172, 1146, 1031, 888, 756, 720 cm−1; HRMS (CI+) m/z 673.4946 (M+H+, C43H65N2O4, requires 673.4944).

1. temperatureThe reaction was cooled to 22° C.
2. customDMF was removed in vacuo
3. additionTo the resulting residue was added CH2Cl2 (10 mL)
4. customThe insoluble material was removed by filtration
5. washwashed with additional CH2Cl2 (2×5 mL)
6. washTo the combined filtrate and wash solutions
7. additioncontaining the crude secondary amine product
8. stirringThe reaction was stirred for 4 h at 22° C.
9. concentrationconcentrated in vacuo