Practical Enzymatic Resolution of Racemic Alcohols and Amines in Organic Solvents^a

Proteases in Organic Synthesis

“…In this original work, kinetic resolution of various amines such as α-methylbenzylamine ( 37 ) was achieved by using an organic solvent system. Later work has used subtilisin, for example, for the production of the pharmaceutically important intermediate ( R )-1-aminoidan ( 38 ) and the chiral resolving agent ( R )-1-(1-naphthyl)ethylamine ( 39 ) . By utilizing a continuous-flow reactor and immobilized subtilisin, the two compounds were resolved in a multigram- and kilogram-scale in ee 's > 98% and yields of 40 and 35%, respectively.…”

Spontaneous Enantiomeric Enrichment of Chiral 1- (1-Naphthyl) Ethylamine

“…Practical methods for their synthesis usually involve multistep transformations starting from chiral natural amino acids, or resolution of racemic mixtures via reaction with a chiral carboxylic acid to form a diastereomeric mixture of salts followed by consecutive fractional crystallizations and recovery of the amine. Enzyme catalyzed aminolysis in organic solvents can provide an alternative method for the preparation of optically active amines such as chiral 1-(1-naphthyl)ethylamine 3,4 . The enantiomeric excess was determined by HPLC chromatographic analysis using Crownpak CR(+) chiral column, solvent mixture of 85% aqueous HClO4 solution (pH 2) and 15% methanol at flow rate of 0.6 ml/minute and detection at 210 nm.…”

Optimization of Process for Enzymatic Resolution of Racemic Amines using Continuous Flow Bioreactor

“…The pioneered work of practical enzymatic resolution of racemic alcohols and amines in organic solvents was also described in the literature 6 . However, the technological aspects of optimization of the process for large-scale production of chiral amines using a continuous flow bioreactor have never been published before.…”