Reacción #704465

Ecuación de reacción

cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine

HBr

→

cis-6-Phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution was cooled
2. 2
   Filtraciónthe resulting white precipitate was collected by filtration
3. 3
   workup.DISSOLUTIONThe hydrobromide salt (9.6 g, 69%) was dissolved in CHCl3 /MeOH
4. 4
   OtroThe layers were separated
5. 5
   Extracciónthe aqueous layer was further extracted with CHCl3 /MeOH
6. 6
   SecadoThe combined organic layers were dried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated
9. 9
   Otroto yield product as an off-white foam

Procedimiento

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): d 7.04 (m, 3H), 6.74 (m, 2H), 6.63 (d, J=8.3 Hz, 2H), 6.50 (m, 3H), 6.28 (d, J=8.6 Hz, 2H), 4.14 (d, J=4.9 Hz, 1H), 3.94 (t, J=5.3 Hz, 2H), 3.24 (dd, J=12.5, 4.1 Hz, 1H), 2.95 (m, 4H), 2.78 (m, 4H), 2.14 (m, 1H), 1.88 (m, 4H), 1.68 (m, 1H).

Fuente