Structural Aspects of the Enantioselectivity of Tartrates with α-Amino-alcohol Salts. Part II. Crystal structures of (1R, 2S)-norephedrine hydrochloride and (1R, 2R)- norpseudoephedrine hydrochloride

✍ Scribed by Martin Egli; Max Dobler

• Publisher: John Wiley and Sons
• Year: 1989
• Tongue: German
• Weight: 275 KB
• Volume: 72
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19890720533

✦ Synopsis

Enantioselective host-guest complexes between a-amino-alcohol salts and chiral tartrates can not be crystallised up to now. To study structural aspects of their enantioselectivity, crystal structures of the components were determined. Norephedrine was used as a reference guest a-amino-alcohol. (1R,2S)-Norephedrine hydrochloride (monoclinic, space group P2,, Z = 4, a = 8.455, b = 10.331, c = 12.570 A, p = 107.45") and (lR,2R)-norpseudoephednne hydrochloride (monoclinic, space group P2,, Z = 2, a = 5.493, b = 8.052, c = 11.986 A, p = 104.62") both adopt M-synclinal conformations with respect to the ammonium and hydroxy groups. Rather short intramolecular N.-0 distances indicate interaction between ammonium and hydroxy groups.