Details for Patent: 9,546,161

Title:	Synthesis of UDP-glucose: N-acylsphingosine glucosyl transferase inhibitors
Abstract:	Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.
Inventor(s):	Hirth; Bradford H. (Littleton, MA), Siegel; Craig (Woburn, MA)
Assignee:	Genzyme Corporation (Cambridge, MA)
Filing Date:	Jun 26, 2014
Application Number:	14/315,453
Claims:	1. A method of preparing an amine compound represented by the following structural formula: ##STR00032## wherein: R.sub.1 is a substituted or unsubstituted aromatic group; R.sub.2 and R.sub.3 are independently --H, a substituted or unsubstituted aliphatic group or, taken together with the nitrogen atom to which they are bonded, are a substituted or unsubstituted non-aromatic heterocyclic ring; and R.sub.5 is a substituted or unsubstituted aromatic group, said method comprising the step of reacting a cyclic starting material with HNR.sub.2R.sub.3, said cyclic starting material being represented by the following structural formula: ##STR00033## thereby forming an intermediate represented by the following structural formula: ##STR00034## hydrolyzing the amino acetal group of the intermediate, thereby forming the acyclic compound represented by the following structural formula: ##STR00035## and reacting the acyclic compound with an amide reducing agent, thereby forming the amine compound. 2. The method of claim 1 wherein the amide reducing agent is lithium aluminum hydride. 3. The method of claim 1 wherein the amide reducing agent is borane tetrahydrofuran.