An Improved and Plant Viable Synthesis of Vitamin K1
Prasad Panchabhai
API Research Centre, Emcure Pharmaceutical Limited, Hinjawadi, Pune 411057, India and Department of Chemistry, Annamalai University, Annamalai Nagar, Chidambaram, India.
Neelakandan Kaliaperumal
API Research Centre, Emcure Pharmaceutical Limited, Hinjawadi, Pune 411057, India.
Gopalakrishnan Mannathusamy
Department of Chemistry, Annamalai University, Annamalai Nagar, Chidambaram, India.
Anbuselvan Chinnadurai *
Department of Chemistry, Annamalai University, Annamalai Nagar, Chidambaram, India.
*Author to whom correspondence should be addressed.
Abstract
An improved and simplified process of vitamin K1 preparation. The article confers the new reagent BF3. Acetic acid complex as a condensation reagent for phytol with compound III in vitamin K1 synthesis, which eludes the use of ethereal reagent and make the process hazard free. Further innovation presents base catalyzed synthesis of vitamin K1 which is an oxidative product of compound IV. Sodium methoxide base is used in synthesis which eliminates use of metal oxidant, costly and hazardous reagent. The new approach ensures the non-generation of epoxide impurity (V) which tends to form during Ag2O catalyzed synthesis. Finally, article also focused on formation and conformation of 7R and 11R diastereomeric centers and ensure the formation of vitamin k1 with desired stereochemistry also article submit proof of concept and supporting literature survey for desired stereochemistry.
Keywords: Acetyl chloride and zinc dust, BF3 acetic acid, Sodium methoxide, silica gel, desired diastereomer C7 and C11, “Z” isomer content, diastereomeric centers (7R and 11R)