Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1-Benzyl-3-pyrrolidinone | HCID 69890 | — |
| Reactant | (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal | HCID 107526 | — |
| Reactant | Nadh | HCID 439153 | — |
| Product | N-benzyl-3-pyrrolidinol | HCID 69889 | 96% |
Reaction Steps
The culture of the recombinant Escherichia coli HB101(pNTDRG1) as obtained in Example 8 was subjected to ultrasonic cell disruption using SONIFIRE 250 (product of BRANSON). To 20 ml of this cell disruption fluid, there were added 2 g of glucose, 1 mg of NAD and 1 g of N-benzyl-3-pyrrolidinone. This reaction mixture was stirred at 30° C. for 18 hours under a nitrogen atmosphere while adjusting the pH to 6.5 by adding 5 M hydrochloric acid and sodium hydroxide solution. After completion of the reaction, 2 ml of 5 M sodium hydroxide solution was added, and this reaction mixture was extracted with toluene. The solvent was then removed from the extract by an evaporator, and the extract was analyzed. Then, N-benzyl-3-pyrrolidinol was obtained in 96% yield. The N-benzyl-3-pyrrolidinol formed on that occasion was the R form with an optical purity of 99.9% ee.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07220564B2 |
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| Source dataset | uspto-grants-2007_05 |
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| ORD ID | ord-c3a069c483254478bd52c2c0462b19b2 |
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| Source note | uspto-grants-2007_05 |
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