1026046-35-4

Upstream product

• 78-77-3 Isobutyl bromide 
• 186521-87-9 1-(4-Chloro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-cyclobutanecarbonitrile 
• 140-53-4 p-chlorobenzyl cyanide 
• 485828-45-3 1-(4-chlorophenyl)-3-hydroxycyclobutane-1-carbonitrile 
• 26562-22-1 2-<2-Bromo-1-(bromomethyl)ethoxy>tetrahydropyran 
• 110-87-2 3,4-dihydro-2H-pyran 

Relevant academic research and scientific papers

Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites

Synthetic routes to N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine (sibutramine) 1 and its demethylated and hydroxylated human metabolites N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methyibutyl}-N-methylamine2, 1-[1-(4-chiorophenyl)cyclobutyl]-3-methylbutylamine 3, 4-amino-4-[1-(4-chlorophenyl)cyclobutyl]-2-methylbutan-1-ol 4 and c-3-(1-amino-3-methylbutyl)-3-(4-chlorophenyl)cyclobutan-r-1-ol 5a are described. Key steps are tandem Grignard-reduction reactions on 1-(4-chlorophenyl)cyclobutanecarbonitrile 7 and its 3-(tetrahydropyran-2-yloxy)-substituted analogue 14 and a convenient one-pot conversion of 4-chlorophenylacetonitrile 6 into the 3-hydroxycyclobutanecarbonitrile 13.