Hydrochloric Acid → N-benzyl-3-pyrrolidinol

HRID 1796895Notes

Reaction equation

HRID 1796895 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.[CH2:61]([N:68]1[CH2:72][CH2:71][C:70](=[O:73])[CH2:69]1)[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1.Cl.[OH-].[Na+]>>[CH2:61]([N:68]1[CH2:72][CH2:71][CH:70]([OH:73])[CH2:69]1)[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14798Sodium Hydroxide2×HCID 698901-Benzyl-3-pyrrolidinone3×HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×

Product 1

HCID 69889N-benzyl-3-pyrrolidinolYield 74%

Conditions

Temperature
30 °C

Procedure

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.

Workup

  1. customThe culture fluid of the recombinant E.coli HB101 (pTSBH) obtained in Example 9
  2. additionwas added
  3. stirringstirring
  4. additionwas added
  5. extractionthe mixture was extracted with toluene
  6. customthe solvent was removed
  7. extractionAnalysis of the resulting extract
  8. customwas obtained in 74% yield

Sources & evidence

ORD record
ord-d09628438ff14473857268232625316e
Source dataset
uspto-grants-2006_04
Patent number
US07033808B2

Reaction notes

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