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Adamantane formaldehyde synthetic method suitable for industrial production

The technology of a kind of adamantane formaldehyde and synthesis method is applied in the field of industrial synthesis of adamantane formaldehyde for synthesizing saxagliptin intermediate, which can solve the problems of being unsuitable for industrial production, difficult to operate in industrial production, and harsh reaction conditions, etc., so as to achieve easy separation, The effect of mild reaction conditions and easy access to solvents

Inactive Publication Date: 2012-08-01
TIANJIN WEIJIE TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 1. The reaction conditions are relatively harsh, requiring a low temperature of -78°C, which is difficult to meet the requirements in industry
[0008] 2. The reaction solvent dichloromethane needs to be absolutely anhydrous, which is not suitable for industrial production
[0009] 3. Post-treatment requires column chromatography separation and purification, which is difficult to operate in industrial production

Method used

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  • Adamantane formaldehyde synthetic method suitable for industrial production
  • Adamantane formaldehyde synthetic method suitable for industrial production
  • Adamantane formaldehyde synthetic method suitable for industrial production

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Under nitrogen protection, add 1L dichloromethane, 100g adamantane methanol, 168g silica gel, and then add 168g PCC oxidant to a 2L four-necked flask equipped with an electric stirrer, keep the temperature at 20-25°C, react for 3 hours, and filter with suction 100g silica gel and 50g calcium hydroxide were added to the filtrate, stirred at room temperature for 1 hour, suction filtered, and the filtrate was evaporated to dryness under reduced pressure to obtain 75g of adamantane formaldehyde white solid, yield 76%, purity 97% (GC, normalization method) .

[0022] The reaction formula is as follows:

[0023]

Embodiment 2

[0025] Add 15L of dichloromethane, 1kg of adamantane methanol, 1.5kg of diatomaceous earth into a 50L reaction kettle equipped with an electric stirrer, and then add 1.5kg of PCC oxidant, keep the temperature at 25-30°C, react for 2 hours, and filter with suction. Add 1kg silica gel and 0.8kg calcium hydroxide in the filtrate, stir 1 hour at room temperature, suction filtration, the filtrate is evaporated to dryness under reduced pressure, obtains adamantane formaldehyde white solid 0.8kg, yield 80%, purity 96% (GC, normalized Law).

Embodiment 3

[0027] Add 240kg of dichloromethane into a 300L reactor, add 12kg of adamantane methanol, 20kg of silica gel under stirring, and pass through the jacket with ice brine, lower the liquid temperature to 5-10°C, then add 20kg of PCC oxidant in batches, and react for 1 hour at room temperature , filter, add 12kg silica gel and 6kg calcium hydroxide to the filtrate, keep the temperature at 30-35°C, react for 1 hour under stirring, filter, wash the filtrate with 3% aqueous hydrochloric acid, wash with saturated saline, separate liquid, organic phase The solvent was distilled off under reduced pressure to obtain 8.7 kg of adamantane formaldehyde as a white solid, with a yield of 84% and a purity of 98% (GC, normalization method).

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Abstract

An adamantane formaldehyde synthetic method suitable for industrial production includes that an adamantane methanol is used as a raw material, a dichloromethane is used as a solvent, a pyridinium chlorochromate (PCC) is used as an oxidizing agent, simultaneously diatomites or silica gels are added to be used as adsorbing agents, a reaction is performed at the temperature of 5 DEG C to 40 DEG C for one to three hours, then post-processing is performed by adding calcium hydroxides and the silica gels or the diatomites in a reaction liquid, and the adamantane formaldehyde is obtained. By means of the adamantane formaldehyde synthetic method suitable for industrial production, the PCC is used for oxidizing the adamantane methanol to obtain the adamantane formaldehyde, and the reaction is performed at room temperature so that reaction conditions are mild. Besides, the used solvent is easy to obtain, the operation process is simple, the separation is convenient, and the yield is high, thereby the adamantane formaldehyde synthetic method is successfully applied to industrial production of onglyza at present.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to an industrial synthesis method of adamantane carboxaldehyde used for synthesizing a saxagliptin intermediate. Background technique [0002] Saxagliptin ONGLYZA TM (saxagliptin Saxagliptin Tablets) is a high-efficiency dipeptidyl peptidase-4 (Dipeptidyl Peptidase 4, DPP-4) inhibitor, which can increase endogenous glucagon by selectively inhibiting DPP-4 Glucagon-like Peptide-1 (GLP-1) and Glucose-dependent Insulinotropic Peptide (GIP) levels, thereby regulating blood sugar. [0003] On the eve of World Diabetes Day in 2010, Bristol-Myers Squibb and AstraZeneca jointly announced that the world's first hypoglycemic drug sand based on the mechanism of incretin was jointly developed by two global pharmaceutical companies. Gliptin has been approved for marketing in 46 countries including the United States, India and many countries in the European Union. Currently, China is still in ...

Claims

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Application Information

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IPC IPC(8): C07C47/347C07C45/29
Inventor 宋洪海许野
Owner TIANJIN WEIJIE TECH
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