This patent is entitled “Process for production of aralkyloxypyrrolidine derivative “. The reaction shown above is the O-benzylation of the secondary alcohol of hydroxypyrrolidine. TBAB is used as the catalyst and is probably forming a bit of benzyl bromide in-situ that co-catalyzes the reaction.
The inventors state that they ran the reaction until the starting material (protected hydroxypyrrolidine) was reduced to 1.3%. Even with the high but purposely incomplete conversion, they achieved a yield of 97%.
In an earlier example in the patent, the inventors used PTC with an iodide co-catalyst and ran the reaction at a lower NaOH concentration and lower temperature. There are several ways to use PTC effectively for this reaction.
If you or your company can benefit from achieving higher process performance in a shorter development time for this PTC reaction or any other reaction, by having access to the best PTC expertise available, NOW CONTACT Marc Halpern to inquire about using phase-transfer catalysis to achieve low-cost high-performance green chemistry. Remember, PTC excels in thousands of reactions in more than 30 reaction categories including strong base reactions, nucleophilic substitutions, oxidations and reductions
If you’re not sure if PTC can help your reaction, now fill out the PTC Project Evaluation Form and E-mail a scanned copy to Marc Halpern or send it by fax to Dr. Halpern at +1 856-222-1124. If your company does not have a secrecy agreement with PTC Organics Inc. already in place, please use “R-groups” instead of the exact chemical structures.
PTC Etherification in Examples 2 and 3
About Marc Halpern
Dr. Halpern is founder and president of PTC Organics, Inc., the only company dedicated exclusively to developing low-cost high-performance green chemistry processes for the manufacture of organic chemicals using Phase Transfer Catalysis. Dr. Halpern has innovated PTC breakthroughs for pharmaceuticals, agrochemicals, petrochemicals, monomers, polymers, flavors & fragrances, dyes & pigments and solvents. Dr. Halpern has provided PTC services on-site at more than 260 industrial process R&D departments in 37 countries and has helped chemical companies save > $200 million. Dr. Halpern co-authored five books including the best-selling “Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives” and has presented the 2-day course “Practical Phase-Transfer Catalysis” at 50 locations in the US, Europe and Asia.
Dr. Halpern founded the journal “Industrial Phase-Transfer Catalysis” and “The PTC Tip of the Month” enjoyed by 2,100 qualified subscribers, now beyond 130 issues. In 2014, Dr. Halpern is celebrating his 30th year in the chemical industry, including serving as a process chemist at Dow Chemical, a supervisor of process chemistry at ICI, Director of R&D at Sybron Chemicals and founder and president of PTC Organics Inc. (15 years) and PTC Communications Inc. (20 years). Dr. Halpern also co-founded PTC Interface Inc. in 1989 and PTC Value Recovery Inc. in 1999. His academic breakthroughs include the PTC pKa Guidelines, the q-value for quat accessibility and he has achieved industrial PTC breakthroughs for a dozen strong base reactions as well as esterifications, transesterifications, epoxidations and chloromethylations plus contributed to more than 100 other industrial PTC process development projects.
Dr. Halpern has dedicated his adult life to his family and to phase-transfer catalysis (in that order!).
