Diethyl Ether → 1-(2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidin-4-ol

Reaction equation

[Al+3:27].[CH3:32][CH2:33][O:34][CH2:35][CH3:36].[Cl:1][c:2]1[cH:3][c:4]2[c:13]([cH:14][cH:15]1)[CH:12]1[c:11]3[c:6]([cH:7][cH:8][cH:9][cH:10]3)[C:5]2([C:17](=[O:18])[N:19]2[CH2:20][CH2:21][CH:22]([OH:25])[CH2:23][CH2:24]2)[CH2:16]1.[H-:26].[H-:29].[H-:30].[H-:31].[Li+:28]>>[Cl:1][c:2]1[cH:3][c:4]2[c:13]([cH:14][cH:15]1)[CH:12]1[c:11]3[c:6]([cH:7][cH:8][cH:9][cH:10]3)[C:5]2([CH2:17][N:19]2[CH2:20][CH2:21][CH:22]([OH:25])[CH2:23][CH2:24]2)[CH2:16]1