| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348548 | Tetrahedron: Asymmetry | 2006 | 6 Pages |
Norephedrine has been efficiently converted into the corresponding diastereomer pseudonorephedrine using a three step, one-pot reaction. The three step process involves treatment of norephedrine with di-tert-butyl dicarbonate (Boc2O); cyclization by way of mesylate formation at the alcohol; and lithium hydroxide mediated hydrolysis of the oxazolidinone. The diastereomeric purity was determined by HPLC and the enantiomeric purity was determined by optical activity measurements and chiral stationary phase HPLC analysis of the pseudonorephedrine oxazolidinone derivatives.
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(1S,2S)-2-Amino-1-phenyl-1-propanolC9H13NO[α]D28=+31.8 (c 3.49, EtOH)Source of chirality: (1R,2S)-norephedrineAbsolute configuration: (1S,2S)
(4S,5S)-4-Methyl-5-phenyl-2-oxazolidinoneC10H11NO2[α]D29=+21.6 (c 2.3, CHCl3)Source of chirality: (1R,2S)-norephedrineAbsolute configuration: (1S,2S)
(1R,2R)-2-Amino-1-phenyl-1-propanolC9H13NO[α]D28=-31.4 (c 3.49, EtOH)Source of chirality: (1S,2R)-norephedrineAbsolute configuration: (1R,2R)
