Week 2: Successes and Challenges in Initial Reactions

This week in lab provided both challenges and successes in my project. The goal for the week was to produce enough of the core material so that I could run new reactions in the upcoming weeks. While I was able to synthesize the product, the yield for the three reactions was smaller than hoped for and set me back a little bit. However, the point of research is to try many things in order to determine what works best, so the bumps in the road will help me to determine efficiency for these reactions.

The reactions run this week follow the reaction scheme displayed below. It is a three reaction process to synthesize the pyrrolodiketopiperzine. initial procedureThe first reaction is called a dibal reduction which uses a reagent called dibal to form an aldehyde product. This reaction was run on a larger scale than previous and produced a yield of about 60%. The second reaction is called an aldol condensation which forms a bond between the aldehyde and the diketopiperazine. The reaction resulted in the production of the wanted product as well as week2 blogthe isomer in a yield of about 40%. An isomer is a molecule with the same chemical formula but the structural confirmation is different. Since these molecules are so similar, it is difficult to separate them and therefore the next experiment was run using a mixed product of the two isomers. The final reaction is called a pyrrole condensation which is the ring forming step, creating a pyrrole attached to the diketopiperazine. This reaction also worked but not with the desired efficiency. After the product was purified, there was only about a 20% yield. The reason for the low yield could be connected to the use of the mixed isomer product but it could also be a result of something else. I will be discussing the results with my professor in the upcoming week in order to determine if the same sequence should be repeated or if I should continue forward with my synthesis.

Working in a lab in a research context for the past two weeks has taught me a lot. No matter what the results are each day, it is important to realize that being wrong or things not going as planned is a part of research. The project I am working on does not have a right answer but my goal is to figure out as much as possible with the time I have to work on it. This project has had some quite successful moments and even this week showed that the reactions themselves are working. It just takes time and trials to optimize the reaction conditions and move the project forward.