Octane → (R)-(+)-1-Benzyl-3-pyrrolidinol

Participants

Reaction Steps

It has been found that alkane-degrading microorganisms are excellent biocatalysts for the hydroxylation of N-benzylpyrrolidine to optically active N-benzyl-3-hydroxy-pyrrolidine. Examples are bacteria degrading n-alkane containing 4 or more C-atoms. By screening with a microtiter plate, 25 of a set of 70 strains degrading n-hexane, n-octane, n-decane, or n-dodedane, were found to be able to catalyse this hydroxylation (example 5). The enantioselectivity and relative activity of 14 selected alkane-degrading strains are shown in table 3 (example 6). Hydroxylation of N-benzylpyrrolidine with Pseudomonas putida P1 gave (R)-N-benzyl-3-hydroxypyrrolidine in 62% e.e.; hydroxylation of N-benzylpyrrolidine with the isolate HXN-1100 gave (R)-N-benzyl-3-hydroxypyrrolidine in 70% e.e.; surprisingly, hydroxylation of N-benzylpyrrolidine with the isolate HXN-200 gave (S)-N-benzyl-3-hydroxypyrrolidine in 53% e.e. (Pseudomonas putida P1 was isolated with n-octane as carbon source by van Beilen, J., ETH Zurich; the isolates HXN-1100 and HXN-200 were isolated with n-hexane as carbon source by Engesser, K.-H. and Plaggemeier, Th., University of Stuttgart; all these strains are in the strain collection of institute of Biotechnology, ETH Zurich).

Provenance & Evidence