Réaction #2006452

Équation de réaction

N-Boc-3-piperidinone

D-glucose

L-alanine

pyridoxal phosphate

N-Boc-3-piperidinone

D-glucose

pyridoxal phosphate

→

N-Boc-3-aminopiperidine

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added
2. 2
   workup.ADDITIONwere added
3. 3
   AutreDuring the reaction
4. 4
   Autrethe reaction liquid
5. 5
   workup.ALIQUOTwas sampled
6. 6
   ExtractionFrom the sample, N-Boc-3-aminopiperidine was extracted by the addition of ethyl acetate

Mode opératoire

After two hours in reaction, 1.25 g of N-Boc-3-piperidinone, 1.7 g of D-glucose, 1.0 g of L-alanine, and 3.3 mg of pyridoxal phosphate were added. Further, after five hours in reaction, 1.25 g of N-Boc-3-piperidinone, 1.7 g of D-glucose, and 3.3 mg of pyridoxal phosphate were added. During the reaction, the reaction liquid was sampled. From the sample, N-Boc-3-aminopiperidine 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-aminopiperidine produced was measured by analyzing N-Boc-3-aminopiperidine under the following GC conditions. Further, by the law of the art, N-Boc-3-aminopiperidine 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 23.5 hours in reaction was 3.13 g. The absolute configuration of N-Boc-3-aminopyrrolidine was (S), and the optical purity was not less than 99.9% e.e.

Source