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Method for synthesizing D-proline

A synthesis method and a proline technology are applied in the synthesis field of D-proline, can solve problems such as difficult synthesis, high price of D-proline, unfavorable industrial production, etc., achieve high optical purity, low catalyst amount, low cost effect

Active Publication Date: 2018-03-23
NANJING REDWOOD FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because racemic proline is difficult to synthesize, the resulting D-proline is expensive and unfavorable for industrial production

Method used

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  • Method for synthesizing D-proline
  • Method for synthesizing D-proline
  • Method for synthesizing D-proline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Step (1) synthesis of intermediate Ⅱ

[0028]

[0029] Add 50g of raw material pyrrolidine-2-carbaldehyde, 6.2g of potassium tert-butoxide and 250ml of absolute ethanol into the hydrogenation kettle, stir evenly, then add 0.075g of (R)-SpiroPAP-Me-Ir, seal it; nitrogen replacement 3 times , replaced by hydrogen for 5 times, pressurized to 2-4MPa, fully stirred, and reacted at 20-25°C for 4 hours; hydrogen should be replenished in time to maintain the pressure, and monitored by HPLC to the point where there is no raw material; after taking out the feed liquid, filter it first to obtain a solid as a catalyst It can be used repeatedly; add 1.5g of activated carbon to the filtrate, keep it warm and stir for 30 minutes. After filtering, the filtrate was evaporated to dryness under reduced pressure at 60°C, and taken twice to dryness with a small amount of ethanol to obtain 50.5 g of oily intermediate II, which was set aside.

[0030] Step (2) synthetic D-proline

[0031...

Embodiment 2

[0034] In the D-proline synthesis method, the addition ratio of each raw material is an important factor affecting the yield. Keep other conditions of Example 1 constant, only change the addition ratio of each raw material to prepare D-proline, and the yield situation is as follows:

[0035]

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Abstract

The invention belongs to the technical field of synthesis of chiral organic compounds, and especially relates to a method for synthesizing D-proline. The method comprises the following steps: taking pyrrolidine-2-carbaldehyde, dissolving the pyrrolidine-2-carbaldehyde in an organic solvent, adding a catalyst and an organic alkali potassium t-butoxide, and carrying out an asymmetric catalysis hydrogenation reaction to obtain an intermediate II; and carrying out an oxidation reaction on the intermediate II and an oxidant to obtain the product D-proline III. The method for synthesizing D-prolinehas the following advantages: the use amount of the catalyst is small, and the catalyst can be used repeatedly, so the cost is saved; the solvent used in the synthesis process is a common solvent, sothe method has the characteristics of low cost, non-toxicity, no pollution, greenness and environmental protection; and the synthesis method has a simple process, the yield in the invention is higherthan the yield in the prior art, and the optical purity of the obtained product is high, so the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of chiral organic compounds, in particular to a synthesis method of D-proline. Background technique [0002] D-amino acids are widely found in living matter, and there are various free D-amino acids in some tissues and body fluids of the human body. Recently, it has been found that some kidney diseases are related to the level of D-amino acids in the body, so the study of D-amino acids is very important for understanding certain It is of great significance for some physiological mechanisms, disease pathogenic factors and aging mechanisms, and can also be used for the synthesis of β-lactam antibiotics and physiologically active peptides. At present, most of the production of D-amino acid is to prepare the racemate by synthetic method, and then carry out the resolution to obtain the optical isomer. Therefore, the resolution of racemic amino acids is an important step in the production of D-amino ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16C07D207/08
CPCC07B53/00C07B2200/07C07D207/08C07D207/16
Inventor 吴法浩李钢屈松涛高仰哲陈红玉
Owner NANJING REDWOOD FINE CHEM CO LTD
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