The use of environmental metrics to evaluate green chemistry improvements to the synthesis of (S,S)-reboxetine succinate
2012
Assaf, Georges | Checksfield, Graham | Critcher, Doug | Dunn, Peter J. | Field, Stuart | Harris, Laurence J. | Howard, Roger M. | Scotney, Gemma | Scott, Adam | Mathew, Suju | Walker, Geoffrey M. H. | Wilder, Alexander
The Pfizer Green Chemistry metrics program is described and exemplified with a case history involving the synthesis of (S,S)-reboxetine succinate. The initial route used a classical resolution approach and generated high levels of waste. This route was replaced by an enantiospecific synthesis which used Sharpless epoxidation chemistry, an enzymatic process to selectively protect a primary alcohol and a new efficient method of chiral morpholine construction as key steps. These improvements reduced the levels of waste produced by the synthesis by more than 90%. Detailed metrics starting from a common starting material (trans-cinnamyl alcohol) for all routes of synthesis are presented.
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