Efficient Resolution of Menthylamine with Inexpensive (<i>R</i>,<i>R</i>)‐Tartaric Acid by Dielectrically Controlled Resolution (DCR)

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公開日
2013-12-05
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/ejoc.201301566
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>A practical procedure for the resolution of menthylamine <jats:bold>2</jats:bold> with (<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐tartaric acid [(<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐<jats:bold>3</jats:bold>] as resolving agent is presented. Variation of the solvent system allows both enantiomers of <jats:bold>2</jats:bold> to be selectively crystallized. Performing the resolution in methanol containing 6 % water leads to (–)<jats:bold>‐2·</jats:bold>(<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐<jats:bold>3·</jats:bold>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 (–)<jats:bold>‐2·</jats:bold>(<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐<jats:bold>3·</jats:bold>MeOH salt to be obtained in an overall yield of 22 %; the other salt (+)<jats:bold>‐2·</jats:bold>(<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐<jats:bold>3·</jats:bold>MeOH<jats:bold>·</jats:bold>H<jats:sub>2</jats:sub>O was obtained in 23 % yield. This is another important example of the dielectrically controlled resolution of an interesting amine by using inexpensive (<jats:italic>R</jats:italic>,<jats:italic>R</jats:italic>)‐tartaric acid as resolving agent.</jats:p>

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