A USEFUL ROUTE TO BOTH ENANTIOMERS OF 1-AMINO-2-ALKANOLS - SYNTHESIS OF 1-AMINO-3-METHYL-2-BUTANOL FROM VALINE

A multistep synthesis of (S)-1-amino-3-methyl-2-butanol (9) from D-val ine (3) is reported. The enantiomeric purity of (S)-9 (97.2 +/- 0.2% e e) is determined by GC of the derivative, 5-isopropyloxazolidin-2-one (2) on both L-and D-Chirasil-Val. (R)-9 is prepared from L-valine in t he same manner; thus, the procedure provides a useful route to both en antiomers of 1-amino-2-alkanols, starting from L- and D-amino acids, r espectively.