A Useful Route to Both Enantiomers of 1-Amino-2-alkanols: Synthesis of 1-Amino- 3-methyl-2-butanol from Valine
25 April 2002 (online)
A multistep synthesis of (S)-1-amino-3-methyl-2-butanol (9) from D-valine (3) is reported. The enantiomeric purity of (S)-9 (97.2 ± 0.2%percnt; ee) 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 the same manner; thus, the procedure provides a useful route to both enantiomers of 1-amino-2-alkanols, starting from L- and D-amino acids, respectively.