Synthesis method of (R)-5-methylpyrrolidone-2-one

A technology of methylpyrrolidone and synthetic method, which is applied in the direction of organic chemistry, organic chemistry, etc., can solve the problems of expensive raw materials, poor universality, and high development difficulty, and achieve high yield, low raw material price, and atom utilization high rate effect
CN110845385AActive Publication Date: 2020-02-28SUZHOU UUGENE BIOPHARMA
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
SUZHOU UUGENE BIOPHARMA
Publication Date
2020-02-28

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Abstract

The invention discloses a synthesis method of (R)-5-methylpyrrolidone-2-one. The synthesis method comprises following steps: step one, adding methyl levulinate, borane dimethyl sulfide, and a catalystinto a solvent, and carrying out reactions for 1 to 5 hours to obtain (R)-4-hydroxylmethyl pentanoate; step two, adding (R)-4-hydroxylmethyl pentanoate obtained in the step (1) into a reactor, introducing a nitrogen source and Raney nickel into the reactor, and carrying out catalytic reactions under a pressurized condition to obtain (R)-4-aminomethyl pentanoate; step three, adding (R)-4-aminomethyl pentanoate into a solvent, adding an alkaline catalyst, raising the temperature to 30-80 DEG C, and carrying out reactions for 0.5 to 5 hours to obtain the target product (R)-5-methylpyrrolidone-2-one; wherein the solvent in the step (1) is one or more of dichloromethane, toluene, dimethyl formamide, dimethyl sulfoxide, dichloromethane, and tetrahydrofuran. The synthesis method has the advantages of easily available and cheap raw materials, high atom utilization rate, high purity, easy purification, and high yield, and the chiral center does not need to be splitted.
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Description

technical field

[0001] The invention belongs to the technical field of pharmaceutical synthesis, in particular to a method for synthesizing (R)-5-methylpyrrolidone-2-one. Background technique

[0002] (R)-5-Methylpyrrolidone-2-one, the chemical formula is:

[0003]

[0004] (R)-5-Methylpyrrolidone-2-one is an intermediate of the heart failure drug sacubitril.

[0005] Sacubitril, the original research company is Novartis, listing time: FDA 2015 / 7 / 7, EMA2015 / 11 / 19, indications: sacubitril combined with valsartan for the treatment of heart failure. Heart failure (heart failure) refers to the failure of the systolic function and / or diastolic function of the heart to fully discharge the venous blood back to the heart, resulting in blood stasis in the venous system and insufficient blood perfusion in the arterial system, thereby causing the heart Circulatory disorder syndrome, which is manifested as pulmonary congestion and vena cava congestion in this disorder syndrome clus...

Claims

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