0000000001299677
AUTHOR
Magdalena Schmitt
Efficient Resolution of Menthylamine with Inexpensive (R,R)-Tartaric Acid by Dielectrically Controlled Resolution (DCR)
A practical procedure for the resolution of menthylamine 2 with (R,R)-tartaric acid [(R,R)-3] as resolving agent is presented. Variation of the solvent system allows both enantiomers of 2 to be selectively crystallized. Performing the resolution in methanol containing 6 % water leads to (–)-2·(R,R)-3·MeOH. The other, less-soluble diastereomeric salt is obtained by applying a solvent system consisting of methanol with 19 % water with a yield of 14 %. Subsequent basic workup with aqueous sodium hydroxide gave the free menthylamine compounds. Further workup of the mother liquors and an additional recrystallization step allowed the (–)-2·(R,R)-3·MeOH salt to be obtained in an overall yield of 2…
CCDC 966732: Experimental Crystal Structure Determination
Related Article: Magdalena Schmitt, Dieter Schollmeyer, Siegfried R. Waldvogel|2014|Eur.J.Org.Chem.|2014|1007|doi:10.1002/ejoc.201301566
CCDC 966733: Experimental Crystal Structure Determination
Related Article: Magdalena Schmitt, Dieter Schollmeyer, Siegfried R. Waldvogel|2014|Eur.J.Org.Chem.|2014|1007|doi:10.1002/ejoc.201301566