Pyridoxal 5'-phosphate → 1-Boc-3-aminopyrrolidine

HRID 1919268Notes

Reaction equation

HRID 1919268 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[NH2:26][C@H](C(O)=O)C.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O.C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1>>[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH2:26])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 5

HCID 1051Pyridoxal 5'-phosphate3×HCID 5893Nadide (JAN/USAN/INN)HCID 5950L-AlanineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal3×HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylate3×

Product 1

HCID 27563701-Boc-3-aminopyrrolidine

Procedure

After 2.5 hours in reaction, 0.625 g of N-Boc-3-pyrrolidinone, 0.91 g of D-glucose, 1.8 g of L-alanine, and 3.3 mg of pyridoxal phosphate were added. Further, after five hours in reaction, 0.625 g of N-Boc-3-pyrrolidinone, 0.91 g of D-glucose, and 3.3 mg of pyridoxal phosphate were added. Furthermore, after nine hours in reaction, 0.25 g of N-Boc-3-pyrrolidinone, 0.36 g of D-glucose, 19 mg of NAD+, and 3.3 mg of pyridoxal phosphate were added. During the reaction, the reaction liquid was sampled. From the sample, N-Boc-3-aminopyrrolidine was extracted by the addition of ethyl acetate after basifying the sample with 6 N aqueous solution of sodium hydroxide. The amount of N-Boc-3-aminopyrrolidine produced was measured by analyzing N-Boc-3-aminopyrrolidine under the following GC conditions. Further, by the law of the art, N-Boc-3-aminopyrrolidine thus obtained was acted on by 3,5-dinitrobenzyl chloride to form a dinitrobenzyl derivative. After that, the dinitrobenzyl derivative was analyzed under the following HPLC conditions, whereby the optical purity thereof was measured. In the result, the amount of N-Boc-3-aminopyrrolidine produced after 23 hours in reaction was 2.14 g. The absolute configuration of N-Boc-3-aminopyrrolidine was (S), and the optical purity was 99.4% e.e.

Workup

  1. additionwere added
  2. additionwere added
  3. additionwere added
  4. customDuring the reaction
  5. customthe reaction liquid
  6. aliquotwas sampled
  7. extractionFrom the sample, N-Boc-3-aminopyrrolidine was extracted by the addition of ethyl acetate

Sources & evidence

ORD record
ord-05c7a7d35dae46c982a00b13e58ad6f4
Source dataset
uspto-grants-2012_05
Patent number
US08168412B2

Reaction notes

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