反応 #1909796

ord-99aefd1c7bb849d7b38987aea6b79e00

反応方程式

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

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他was hydrogenated on a Parr shaker at 50° C.
  2. 2
    ろ過The catalyst was filtered off with the aid of Celite
  3. 3
    その他the solvents were removed in vacuo
  4. 4
    workup.DISSOLUTIONThe resulting white solid was dissolved in CH2Cl2
  5. 5
    洗浄the solution was washed with saturated NaHCO3 (aq)
  6. 6
    乾燥The organic solution was dried (MgSO4)
  7. 7
    ろ過filtered
  8. 8
    濃縮concentrated

実験手順

1-[2-[4-(6-Methoxy-2-phenyl-3,4-dihydronaphthalen 1yl)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 (0.34 MPa) 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 saturated NaHCO3 (aq). The organic solution was dried (MgSO4), filtered, and concentrated to yield an off-white solid (62.6 g, 90%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07037530B2uspto-grants-2006_05