3-Bromoanisole → (1RS,2RS,4SR)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-phenylethyl-cyclohexanol hydrochloride

HRID 2392758Notes

Reaction equation

HRID 2392758 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][C:7]1=[O:20])[CH3:4].Br[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1>>[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9][CH2:8][C:7]1([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[OH:20])[CH3:4]

Participants

3

Reactant 2

HCID 169713-BromoanisoleHCID 189804162-Dimethylaminomethyl-4-(phenethyl)-cyclohexanone hydrochloride

Product 1

HCID 67642006(1RS,2RS,4SR)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-phenylethyl-cyclohexanol hydrochlorideYield 40%

Procedure

The base of compound (48) was reacted with 1-bromo-3-methoxy-benzene corresponding to the conditions described in Example 1. The base obtained was purified firstly with 7:1 ether/methanol via a silica gel column and subsequently via HPLC. It was taken up in 2-butanone and trimethylchlorosilane/water was added, with the addition of ether if necessary. Compound (45) was obtained in a yield of 40% theoretical.

Workup

  1. customThe base obtained
  2. customwas purified firstly with 7:1 ether/methanol via a silica gel column and subsequently via HPLC
  3. additiontrimethylchlorosilane/water was added, with the addition of ether if necessary

Sources & evidence

ORD record
ord-12bc53f40f4a406cb733b3a89d7c6082
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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