Abstract
Chiral mandelic acid (S)-1, which is an important precursor for stereoselective transformations and a versatile intermediate for pharmaceuticals, was resolved with the Pope and Peachey method. Enantiopure 1-amino-3-phenoxypropan-2-ol (S)-2, a key intermediate for pharmaceuticals, was used to resolve rac-mandelic acid rac-1 successfully for the first time. The less soluble salt (S)-1·(S)-2·H2O could be obtained in 77% yield and 98% de (E 75%) using (S)-2 and LiOH in water. The crystal structure of the less soluble salt (S)-1·(S)-2·H2O showed that the water molecule played a key role in forming the crystals.
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