Réaction #54346

Équation de réaction

3-phenylpropylmagnesium bromide

1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone

tetrahydrofuran

ammonium chloride

tetrahydrofuran

→

title compound

1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol

Solvants

ether

Conditions de réaction

Traitement

1. 1
   AutreTo a 0° C.
2. 2
   workup.ADDITIONis then added to 250 ml
3. 3
   SéchageThe ether phase is dried over magnesium sulfate
4. 4
   Autreevaporated
5. 5
   AutreThe residue is purified via column chromatography on 200 g
6. 6
   Lavageof silica gel eluted with 50% ether-cyclohexane

Mode opératoire

To a 0° C. solution of 7.0 mmols. of 3-phenylpropylmagnesium bromide in 7 ml. of tetrahydrofuran is slowly added a solution of 2.48 g. (5.0 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone in 10 ml. of tetrahydrofuran. The resultant mixture is stirred for one hour and is then added to 250 ml. of saturated ammonium chloride-250 ml. ether. The ether phase is dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 200 g. of silica gel eluted with 50% ether-cyclohexane to yield the title compound.

Source