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

HRID 2392744Notes

Reaction equation

HRID 2392744 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][CH2:8][C:7]1=[O:17])[CH3:4].Br[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1>>[ClH:1].[CH3:4][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([O:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:9][CH2:8][C:7]1([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[OH:17])[CH3:2]

Participants

3

Reactant 2

HCID 169713-BromoanisoleHCID 189805002-Dimethylaminomethyl-4-isobutoxy-cyclohexanone hydrochloride

Product 1

HCID 18980492(1RS,2RS,4SR)-2-dimethylaminomethyl-4-isobutoxy-1-(3-methoxy-phenyl)-cyclohexanol hydrochlorideYield 38%

Procedure

The base of compound (22) was reacted with 1-bromo-3-methoxy-benzene corresponding to the conditions described in Example 1. The base obtained was purified with 1:1 ethyl acetate/methanol via a silica gel column, and was taken up in ether. After adding trimethylchlorosilane/water, compound (20) was obtained in a yield of 38% theoretical.

Workup

  1. customThe base obtained
  2. customwas purified with 1:1 ethyl acetate/methanol via a silica gel column
  3. additionAfter adding trimethylchlorosilane/water

Sources & evidence

ORD record
ord-91ca4fe8121d4a92b902973a702f38db
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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