O-Benzyl derivatives of (S)-(+) and (R)-(-)-2-aminobutan-1-ol as new resolving agents for racemic acids. Practical resolutions of N-acyl derivatives of phenylglycine and 4-hydroxyphenylglycine

Article abstract of DOI:10.1016/S0040-4039(00)60491-4

Treatment of the readily available (S)-(+) and (R)-(-)-2-aminobutan-1-ol 1 with sodium hydride followed by benzyl chloride, or a substituted benzyl halide, afforded the corresponding O-benzyl bases 2-5 in high yields. These new bases are recommended for the large scale resolution of racemic acids. For instance, they proved efficient for the practical resolution of N-acetylphenylglycine (±)-7, N-acetyl-(4-hyroxylphenyl)glycine (±)-9 and N-chloroacetyl-(4-hydroxyphenyl) glycine (±)-10.