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Enantioselective synthesis of (R)- and (S)-N-Boc-morpholine-2-carboxylic acids by enzyme-catalyzed kinetic resolution: application to the synthesis of reboxetine analogs

✍ Scribed by Paul V. Fish; Malcolm Mackenny; Gerwyn Bish; Timothy Buxton; Russell Cave; David Drouard; David Hoople; Alan Jessiman; Duncan Miller; Christelle Pasquinet; Bhairavi Patel; Keith Reeves; Thomas Ryckmans; Melanie Skerten; Florian Wakenhut


Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
163 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis


The (R)-and (S)-N-Boc-morpholine-2-carboxylic acids 9 and 10 were prepared using an enantioselective synthesis employing a highly selective enzyme-catalyzed kinetic resolution of racemic n-butyl 4-benzylmorpholine-2-carboxylate (11) as the key step. Acids 9 and 10 were then converted efficiently and stereoselectively to reboxetine analogs 3 and 4.