HCID 68553217, compound → HCID 9924115, compound

HRID 2244499Notes

Reaction equation

HRID 2244499 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH2:19]([Mg]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([C:6]1([OH:9])[CH2:7][CH2:8][C:3]([N:2]([CH3:1])[CH3:18])([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH2:4][CH2:5]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68553217HCID 68553217, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 9924115HCID 9924115, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.67 g 4-dimethylamino-4-(3-fluorobenzyl)cyclohexanone were reacted with 1.0 molar benzylmagnesium chloride solution in THF analogously to the preparation of 4-dimethylamino-4-(4-fluorobenzyl)-1-phenethylcyclohexanol. After chromatography over silica gel, the nonpolar diastereoisomer of 1-benzyl-4-dimethylamino-4-(3-fluorobenzyl)cyclohexanol obtained was converted into 261 mg of the corresponding hydrochloride as described for example 4.

Sources & evidence

ORD record
ord-dc48d24db6d1482b93b84b6b7483967d
Source dataset
uspto-grants-2010_03
Patent number
US07678834B2

Reaction notes

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