Synthesis of 4-arylpiperidines from 1-benzyl-4-piperidone: Application of the Shapiro reaction and alkenylsilane cross-coupling

ORGN 566

Christie Morrill, cmorril3@prdus.jnj.com and Neelakandha S. Mani, nmani@prdus.jnj.com. Scale-Up Group, Johnson & Johnson Pharmaceutical Research & Development, 3210 Merryfield Row, San Diego, CA 92121-1126
1-Benzyl-3,4-unsaturated-4-piperidinyl benzyldimethylsilane has been prepared and observed to readily undergo palladium-catalyzed cross-coupling reactions with a variety of aryl iodides and aryl bromides to generate 3,4-unsaturated 4-arylpiperidines, often at ambient temperature.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007