Practical syntheses of (S)-N-BOC-2-Hydroxymethylmorpholine 5  has attracted the interest of several research groups. The Lilly Research Laboratories identified 5  as a potential API starting material for a cancer treatment candidate. This required development of a robust process capable of reliably making multi-kilogram amounts of 5  . Our initial process to generate 5  was not robust and provided the product with variable quality and in variable yield. Herein, we report a more efficient and robust process to synthesize 5  through telescoping steps 2 and 3, with more simplified unit operations, chemical use, and more controlled crystallizations, resulting in reliably high yields and potencies of 5 .

Process development for synthesis of (S)-N-BOC-2-Hydroxymethylmorpholine

246th National Meeting (2013)

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