3-Bromophenetole → (1RS,2RS,4SR)-4-(cyclopentylethyl)-2-dimethylaminomethyl-1-(3-ethoxyphenyl)-cyclohexanol hydrochloride
Reaction equation
[ClH:1].[CH:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH3:29])[CH:22]=1>>[ClH:1].[CH:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH3:29])[CH:22]=3)([OH:15])[CH:11]([CH2:16][N:17]([CH3:19])[CH3:18])[CH2:10]2)[CH2:3][CH2:4][CH2:5][CH2:6]1Participants
3
Procedure
The base of compound (56) was reacted with 1-bromo-3-ethoxy-benzene corresponding to the conditions described in Example 1. The base obtained was purified with diisopropyl ether via a silica gel column and was taken up in 2-butanone/ether. After adding trimethylchlorosilane/water, compound (58) was obtained in a yield of 52% theoretical.
Workup
- custom