Hydrochloric Acid → N-benzyl-3-pyrrolidinol

Participants

Reaction Conditions

Reaction Steps

The culture fluid of the recombinant E.coli HB101 (pTSBH) obtained in Example 9 was ultrasonically disrupted using SONIFIRE 250 (product of BRANSON). To 25 ml of this cell disruption fluid were added 1,350 U of glucose dehydrogenase (product of Amano Pharmaceutical), 3.0 g of glucose, 3.0 mg of NADP and 0.25 g of N-benzyl-3-pyrrolidinone. While this reaction mixture was stirred at 30° C. with pH adjusted to 6.5 using 5 M hydrochloric acid or sodium hydroxide, N-benzyl-3-pyrrolidinone was added thereto at an interval of 0.25 g/hour. After addition of a total of 2.0 g of N-benzyl-3-pyrrolidinone, stirring was further continued for 20 hours. After completion of the reaction, 2.5 ml of a 5 M aqueous solution of sodium hydroxide was added, the mixture was extracted with toluene, and the solvent was removed. Analysis of the resulting extract revealed that N-benzyl-3-pyrrolidinol was obtained in 74% yield. The N-benzyl-3-pyrrolidinol produced on that occasion was the S form with an optical purity of not less than 99% ee.

Provenance & Evidence