反应详情

温度

100 °C

A mixture of cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine (12 g, 28 mmol), acetic acid (75 mL), and 48% HBr (75 mL) was heated at 100° C. for 15 h. The solution was cooled and the resulting white precipitate was collected by filtration. The hydrobromide salt (9.6 g, 69%) was dissolved in CHCl3/MeOH and was stirred with satd NaHCO3 (aq). The layers were separated and the aqueous layer was further extracted with CHCl3/MeOH. The combined organic layers were dried (MgSO4), filtered, and concentrated to yield product as an off-white foam. 1H NMR (250 MHz, CDCl3): δ7.04 (m, 3 H), 6.74 (m, 2 H), 6.63 (d, J=8.3 Hz, 2 H), 6.50 (m, 3 H), 6.28 (d, J=8.6 Hz, 2 H), 4.14 (d, J=4.9 Hz, 1 H), 3.94 (t, J=5.3 Hz, 2 H), 3.24 (dd, J=12.5, 4.1 Hz, 1 H), 2.95 (m, 4 H), 2.78 (m, 4 H), 2.14 (m, 1 H), 1.88 (m, 4 H), 1.68 (m, 1 H).

1. temperatureThe solution was cooled
2. filtrationthe resulting white precipitate was collected by filtration
3. dissolutionThe hydrobromide salt (9.6 g, 69%) was dissolved in CHCl3/MeOH
4. customThe layers were separated
5. extractionthe aqueous layer was further extracted with CHCl3/MeOH
6. dry with materialThe combined organic layers were dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield product as an off-white foam