Reacción #77445

Ecuación de reacción

11-Benzyl-5-Ethyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride

ammonium formate

→

solid

Rendimiento 68.0%

5-ETHYL-11-AZA-TRICYCLO[7.3.1.02,7]TRIDECA-2(7),3,5-TRIENE HYDROCHLORIDE

Rendimiento 68.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawarmed
2. 2
   Temperaturato reflux for 15 min
3. 3
   TemperaturaThe mixture was cooled
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   workup.ADDITIONdiluted with sat. aq. Na2CO2 soln
7. 7
   Extracciónand extracted with EtOAc (3×20 mL)
8. 8
   SecadoThe extracts were dried (MgSO4)
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated to an oil (94 mg, 83%)
11. 11
    workup.DISSOLUTIONThis material was dissolved in excess 1N HCl MeOH
12. 12
    Concentraciónconcentrated
13. 13
    OtroRecrystallization from CH2Cl2/Et2O

Procedimiento

11-Benzyl-5-Ethyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride (160 mg, mmol), ammonium formate (220 mg, 3.49 mmol) and 10% Pd(OH)2/C (100 mg) were combined in methanol (MeOH) (5 mL) and warmed to reflux for 15 min. The mixture was cooled, filtered, concentrated, diluted with sat. aq. Na2CO2 soln. and extracted with EtOAc (3×20 mL). The extracts were dried (MgSO4), filtered and concentrated to an oil (94 mg, 83%). (TLC 50% EtOAc/hexanes (NH3) Rf 0.20). 1H NMR (CDCl3) δ 6.90 (d, J=9.0 Hz, 1H). 6.66 (2H), 3.97 (m, 2H), 3.08 (dd, J=18.0, 6.0 Hz, 1H), 2.94 (m, 3H), 2.76-2.65 (3H), 1.96 (m, 2H), 1.88 (d, J=11.0 Hz, 1H), 1.38 (t, J=7.0 Hz, 3H). This material was dissolved in excess 1N HCl MeOH and concentrated. Recrystallization from CH2Cl2/Et2O provided a solid (74 mg, 68%). mp 243-245° C.

Fuente