Sathish K. Boini, K. P. Moder, R. Vaid
Oct 24, 2006
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0
Influential Citations
3
Citations
Journal
Organic Process Research & Development
Abstract
This contribution describes process development leading to the production of 1-(1-pyridin-2-yl methyl-piperidin-4-yl)-1H-indole (11). The title compound 11 was produced via a Leimgruber−Batcho indole synthesis using key intermediates 2-(2,2-dimethoxyethyl)benzenamine (6) and, 1-(2-pyridinylmethyl)-4-piperidinone camphor sulfonate (9). Direct crystallization of 11 from IPA or ethanol−water was developed to provide (11) with <1% impurities and high yield (78%). The combined process leads to a five-step synthesis of 11 that was efficient and reflected Eli Lilly and Company's commitment to implementation of environmental friendly processes whenever feasible.