866083-42-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carbonitrile is used as a key intermediate in the synthesis of Saxagliptin hydrochloride monohydrate, an anti-diabetic drug. It plays a crucial role in a coupling reaction with (S)-phthalimido-(3-hydroxy-adamantan-1-yl)acetic acid, followed by the removal of the phthalimide protecting group and treatment with HCl to yield the final drug product. This application highlights its importance in the development of medications for the treatment of diabetes.

Upstream product

• 361442-57-1 (1S,3S,5S)-tert-butyl-3-cyano-2-azabicyclo[3.1.0]hexane-2-carboxylate 
• 361440-67-7 [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester 
• 32431-85-9 2,5-dibromo-3-fluoro-thiophene 

Relevant academic research and scientific papers

STEROID DERIVATIVE REGULATORS, METHOD FOR PREPARING THE SAME, AND USES THEREOF

The present invention relates to steroid derivative regulators, a method for preparing the same, and uses thereof. Specifically, the present invention relates to a compound as shown in formula (I), a preparation method therefor, a pharmaceutical composition containing the compound, and uses thereof as a regulator of GABA A receptor for treating depression, convulsion, Parkinson's disease, and nervous system diseases, wherein the substituents of the formula (I) are as defined in the description.

Method for preparing saxagliptin

The invention discloses a method for preparing saxagliptin, and belongs to the technical field of drug synthesis. The method comprises the following steps: (a) converting amide on a compound shown ina formula I into cyano and removing Boc groups to obtain a compound shown in a formula II; (b) condensing the compound shown in the formula II and a compound shown in a formula III to obtain a compound shown in a formula IV; and (c) removing Boc groups on the compound shown in the formula IV to obtain a compound shown in a formula V. According to the method, different raw materials and reaction reagents are selected, and a process route is changed, so that four procedures of salifying, condensing, cyanating and de-protecting are shortened into three procedures of cyanating, condensing and de-protecting; meanwhile, cyanating and condensation reaction are realized at the room temperature, the requirements on reaction conditions are reduced, and industrial production can be realized.

Preparation method for synthesizing 2-azabicyclo[4.1.0]heptane-1-carboxylic acid hydrochloride

The invention discloses a preparation method for synthesizing 2-azabicyclo[4.1.0]heptane-1-carboxylic acid hydrochloride. The preparation method comprises the following steps: firstly obtaining a compound III through electrophilic substitution by taking N-substituted-1,2,3,6-tetrahydropyridine (compound II) as a raw material; carrying out cycloaddition reaction of the compound III and a sulfur ylide reagent to obtain a compound IV; finally carrying out deamination protecting group and ester hydrolysis to obtain the 2-azabicyclo[4.1.0]heptane-1-carboxylic acid hydrochloride (compound I).