반응 #77445

반응 방정식

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

ammonium formate

→

solid

수율 68.0%

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

수율 68.0%

용매

methanol

반응 조건

후처리

1. 1
   온도warmed
2. 2
   온도to reflux for 15 min
3. 3
   온도The mixture was cooled
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   workup.ADDITIONdiluted with sat. aq. Na2CO2 soln
7. 7
   추출and extracted with EtOAc (3×20 mL)
8. 8
   건조The extracts were dried (MgSO4)
9. 9
   여과filtered
10. 10
    농축concentrated to an oil (94 mg, 83%)
11. 11
    workup.DISSOLUTIONThis material was dissolved in excess 1N HCl MeOH
12. 12
    농축concentrated
13. 13
    기타Recrystallization from CH2Cl2/Et2O

실험 절차

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.

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