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Synthesis method for (R)-3-amino-1,2,3,4-tetrahydrocarbazole

A synthetic method and tetrahydrocarbazole technology are applied in the field of chemical synthesis of ramatroban pharmaceutical intermediates, which can solve the problems of expensive reagents and low yields, and achieve simple and convenient synthetic methods, mild operating conditions, and high reaction yields. high rate effect

Active Publication Date: 2016-06-22
上海亚兴生物医药科技有限公司
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Problems solved by technology

Solve the technical problems of low yield and expensive reagents in the existing synthesis process

Method used

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  • Synthesis method for (R)-3-amino-1,2,3,4-tetrahydrocarbazole
  • Synthesis method for (R)-3-amino-1,2,3,4-tetrahydrocarbazole
  • Synthesis method for (R)-3-amino-1,2,3,4-tetrahydrocarbazole

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Embodiment Construction

[0033] The technical solution of the present invention is illustrated below through specific examples. The raw materials and reagents used in the present invention are all commercially available.

[0034] 1. Synthesis of Compound 3

[0035] The chemical name of compound 3 in the present invention is: 1-phenyl-2-(1,4-dioxaspiro[4.5]decane-8-ylidene) hydrazine; The chemical name of the raw material compound 1 for synthesizing compound 3 is Phenylhydrazine, compound 2-position 1,4-cyclohexanedione monoethylene glycol ketal; the reaction formula for synthesizing compound 3 is as follows:

[0036]

[0037] The specific preparation process of compound 3 is: in a 3L three-necked flask equipped with a condenser, add 1,4-cyclohexanedione monoethylene glycol ketal (100g, 1eq), 2L of anhydrous toluene and phenylhydrazine respectively (69g, 1eq), stirring and heating up to reflux for 1 hour, TLC detection tracking reaction process, when the raw material disappeared, stop heating. Th...

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Abstract

The invention discloses a method for synthesizing a ramatroban intermediate (R)-3-amino-1,2,3,4-tetrahydrocarbazole. The synthesis method of the present invention is: 1,4-cyclohexanedione monoethylene glycol ketal and phenylhydrazine are condensed through aldehydes, ketones and amines, and then ring-closed to obtain 3,3-vinyldioxy-1,2,4,9 -Tetrahydrocarbazol-3-one, and then remove the protecting group to obtain 1,2,4,9-tetrahydrocarbazol-3-one; 1,2,4,9-tetrahydrocarbazole-3- The ketone is then reacted with O-alkylhydroxylamine hydrochloride to obtain the oxime ether, and the oxime ether can be directly reduced to (R)-3-amino-1,2,3,4-tetrahydrocarbazole by chiral selective reduction at low temperature. The invention of this paper provides a new synthetic route of the important intermediate (R)-3-amino-1,2,3,4-tetrahydrocarbazole of the drug ramatroban. The synthetic method is simple and convenient, the operating conditions are mild, and the reaction The yield is high, and the amplification reaction can be carried out, and can be applied to industrial production.

Description

technical field [0001] The invention relates to a chemical synthesis process of a ramatroban pharmaceutical intermediate, in particular to a synthesis method of (R)-3-amino-1,2,3,4-tetrahydrocarbazole. Background technique [0002] (R)-3-Amino-1,2,3,4-tetrahydrocarbazole is an important intermediate in the synthesis of ramatroban, which is a highly efficient selective thromboxane A2 (TXA2) / prostaglandin Peroxide H2 (PGH2) receptor antagonist that specifically binds to TXA2 receptors in smooth muscle and platelets. It has strong blood vessel and bronchial smooth muscle contraction and platelet activation. The anti-allergic effect of ramatroban is based on the inhibition of vascular permeability and nasal mucosal hypersensitivity and the prevention of other inflammatory reactions, and is especially suitable for the treatment of allergic rhinitis. A good method for synthesizing the compound has broad market prospects. [0003] US Patent 4988820 discloses the synthesis of thi...

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Application Information

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IPC IPC(8): C07D209/88
CPCY02P20/55C07D209/88
Inventor 黄英豪付闪宾
Owner 上海亚兴生物医药科技有限公司
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