反应详情

To the amide from example 25 (27.5 g, 0.092 mol) in dry THF (100 ml) was added borane-methyl sulphide complex (17.5 ml, 0.18 mol) and the reaction mixture was stirred at reflux for 2 hours. The reaction mixture was cooled then quenched with methanol (30 ml). Water (50 ml) and c.HCl (35 ml) were added and the reaction mixture stirred until all bubbling ceased before concentrating in vacuo. To the residue water (250 ml) was added, before basifying by addition of NH4OH (30 ml). The aqueous layer was extracted with ethyl acetate (3×200 ml) and the combined organic extracts dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a white solid (26.1 g, 0.09 mol, 99%). 1H NMR (CD3OD, 400 MHz) δ: 0.95 (t, 3H), 1.58 (q, 2H), 2.62 (m, 2H), 2.81 (m, 2H), 4.72 (dd, 1H), 5.05 (s, 2H), 6.95 (d, 2H), 7.24 (m, 3H), 7.35 (t, 2H), 7.41 (d, 2H). LRMS: m/z 286 (M-H+).

1. temperatureat reflux for 2 hours
2. temperatureThe reaction mixture was cooled
3. customthen quenched with methanol (30 ml)
4. additionHCl (35 ml) were added
5. stirringthe reaction mixture stirred until all bubbling
6. concentrationbefore concentrating in vacuo
7. additionTo the residue water (250 ml) was added
8. additionbefore basifying by addition of NH4OH (30 ml)
9. extractionThe aqueous layer was extracted with ethyl acetate (3×200 ml)
10. dry with materialthe combined organic extracts dried over anhydrous magnesium sulphate
11. filtrationfiltered
12. concentrationconcentrated in vacuo