반응 #704464

ord-f458c9660e514059a80f259346d4d269

반응 방정식

COc1ccc2c(c1)CCC(c1ccccc1)=C2c1ccc(OCCN2CCCC2)cc1.Cl
1-{2-[4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine hydrochloride
COc1ccc2c(c1)CC[C@H](c1ccccc1)[C@@H]2c1ccc(OCCN2CCCC2)cc1
solid
수율 90.4%
COc1ccc2c(c1)CC[C@H](c1ccccc1)[C@@H]2c1ccc(OCCN2CCCC2)cc1
cis-1-{2-[4-(6-Methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine
수율 90.4%

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타was hydrogenated on a Parr shaker at 50° C.
  2. 2
    여과The catalyst was filtered off with the aid of celite
  3. 3
    기타the solvents were removed in vacuo
  4. 4
    workup.DISSOLUTIONThe resulting white solid was dissolved in CH2Cl2
  5. 5
    세척the solution was washed with satd NaHCO3 (aq)
  6. 6
    건조The organic solution was dried (MgSO4)
  7. 7
    여과filtered
  8. 8
    농축concentrated

실험 절차

1-{2-[4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine hydrochloride (nafoxidene hydrochloride) (75 g, 162 mmol) was dissolved in 1000 mL of EtOH and 300 mL of MeOH. Dry Pd(OH)2 on carbon was added and the mixture was hydrogenated on a Parr shaker at 50° C. and 50 psi for 68 h. The catalyst was filtered off with the aid of celite and the solvents were removed in vacuo. The resulting white solid was dissolved in CH2Cl2 and the solution was washed with satd NaHCO3 (aq). The organic solution was dried (MgSO4), filtered, and concentrated to yield an off-white solid (62.6 g, 90%).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05948809uspto-grants-1999_09