3-(Trifluoromethyl)cyclohexanone → (1RS,2RS,5RS)-3-(2-dimethylaminomethyl-1-hydroxy-5-trifluoromethyl-cyclohexyl)-phenol hydrochloride

HRID 1594528Notes

Reaction equation

HRID 1594528 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([F:14])([F:13])[F:12])[CH2:7][C:6]1=[O:15])[CH3:3].FC(F)(F)[CH:18]1[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1.CN(C(Cl)[Cl:31])C>C(#N)C>[ClH:31].[CH3:3][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([F:14])([F:12])[F:13])[CH2:7][C:6]1([C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)[OH:15])[CH3:1]

Participants

5

Reactant 3

HCID 27793553-(Trifluoromethyl)cyclohexanoneHCID 10290805Dimethylaminomethylene chlorideHCID 21705850(2RS,5RS)-2-dimethylaminomethyl-5-trifluoromethyl-cyclohexanone

Product 1

HCID 21705866(1RS,2RS,5RS)-3-(2-dimethylaminomethyl-1-hydroxy-5-trifluoromethyl-cyclohexyl)-phenol hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 5-epimer (27) of compound (25) was prepared, under the conditions given in Example 27, from (2RS,5RS)-2-dimethylaminomethyl-5-trifluoromethyl-cyclohexanone, prepared from 3-trifluoromethyl-cyclohexanone and dimethylaminomethylene chloride in acetonitrile. (27) was obtained in a yield of 27% theoretical and had a melting point of 221°-223° C.

Workup

  1. customThe 5-epimer (27) of compound (25) was prepared, under the conditions

Sources & evidence

ORD record
ord-e2edfb3bf34348ae91b0ec94c5686ac9
Source dataset
uspto-grants-2001_09
Patent number
USRE037355E1

Reaction notes

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