177793-80-5

Basic information

• Product Name: (3S)-N-[[(1S)-1,2,3,4-Tetrahydro-1-naphthalenyl]Methyl]-1-azabicyclo[2.2.2]octan-3-aMine
• Synonyms: (3S)-N-[[(1S)-1,2,3,4-Tetrahydro-1-naphthalenyl]Methyl]-1-azabicyclo[2.2.2]octan-3-aMine;[S-(R*,R*)]-N-[(1,2,3,4-Tetrahydro-1-naphthalenyl)Methyl]-1-azabicyclo[2.2.2]octan-3-aMine;(3S)-N-[[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]methyl]-1-azabicyclo[2.2.2]octan-3-amine
• CAS NO: 177793-80-5
• Molecular Formula: C18H26N2
• Molecular Weight: 270
• Product Categories: Amines;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 177793-80-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S)-N-[[(1S)-1,2,3,4-Tetrahydro-1-naphthalenyl]Methyl]-1-azabicyclo[2.2.2]octan-3-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-N-[[(1S)-1,2,3,4-Tetrahydro-1-naphthalenyl]Methyl]-1-azabicyclo[2.2.2]octan-3-aMine(177793-80-5)
• EPA Substance Registry System: (3S)-N-[[(1S)-1,2,3,4-Tetrahydro-1-naphthalenyl]Methyl]-1-azabicyclo[2.2.2]octan-3-aMine(177793-80-5)

Safety Data

• Hazardous Substances Data: 177793-80-5(Hazardous Substances Data)

Upstream product

• 177793-79-2 N-(1-azabicyclo[2.2.2]oct-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ylcarboxamide 
• 177793-79-2 N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalene-1S-carboxamide 
• 85977-52-2 (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 
• 1914-65-4 tetralin-1-carboxylic acid 
• 50341-99-6 1,2,3,4-tetrahydronaphthalene-1-carbonyl chloride 
• 18278-24-5 (S)-(-)-1,2,3,4-tetrahydro-1-naphthaldehyde 
• 120570-05-0 (S)-3-aminoquinuclidine 
• 80096-46-4 (1,2-dihydronaphthalen-4-yl)methanamine hydrochloride 
• 1193-65-3 3-quinuclidinone hydrochloride 

Downstream Products

• 135729-60-1 palonosetron 
• 135755-51-0 palonosetron hydrochloride 

Relevant articles and documents

Hydrochloric acid palonosetron and intermediate preparation method (by machine translation)

The invention discloses hydrochloric acid palonosetron and intermediate preparation method. The invention provides a preparation method of palonosetron intermediate I, comprises the following steps: in the organic solvent, the presence of a reducing agent, the compound III with the S - 3 - amino quinine cyclic amine reaction of intermediate I Sparrow division of the agar. The invention palonosetron preparation method of the midbody mild reaction conditions, post-processing step is simple, safe operation, the total yield is high, the prepared product has high purity, low production cost, the atom utilization rate is high, and is suitable for industrial production; and palonosetron intermediates of the present invention can be prepared in accordance with the raw materials of the standard of the hydrochloric acid palonosetron. (by machine translation)

A hydrochloric acid palonosetron synthesis method

The invention relates to a new synthetic method of palonosetron hydrochloride, and belongs to the field of pharmaceutical organic synthesis. The synthetic method adopts racemized tetrahydro naphthoic acid as a raw material; a reaction is carried out with thionyl chloride and (S)-3-aminoquinuclidine; after repeated washing, (S,S)-quinuclidine tetrahydronaphthalene carboxamide is obtained; the amide is reacted with sodium borohydride and boron trifluoride diethyl etherate; the product is added into a hydrochloric acid aqueous solution to obtain the palonosetron hydrochloride. According to the method, in the amide synthetic process, ethyl acetate is used as a solvent, which reduces the generation of by-products. In addition, according to the method, in the post-treatment process, impurities are removed by phase transfer, which increases product optical purity; through repeated washing, other impurities generated in the reaction are removed, and high-purity product is obtained.

Synthesis process of palonosetron hydrochloride hydrochloride

The invention discloses a synthesis process of palonosetron hydrochloride hydrochloride. The synthesis process comprises the following steps: S1, performing condensation reduction on 3,4-dihydro-1-naphthalenemethylamine hydrochloride and 3-quinuclidinone hydrochloride which serve as raw materials, thus obtaining a n-butanol solution of N-[(3,4-dihydronaphthalene-1-yl) methyl]-(S)-1-azabicyclo [2.2.2] octane-3-amine; S2, directly adding a catalyst into the n-butanol solution of the N-[(3,4-dihydronaphthalene-1-yl) methyl]-(S)-1-azabicyclo [2.2.2] octane-3-amine for hydrogenation reduction, thus obtaining N-[(1,2,3,4-tetrahydronaphthalene-1-yl) methyl]-(S)-1-azabicyclo [2.2.2] octane-3-amine; S3, performing cyclization on the N-[(1,2,3,4-tetrahydronaphthalene-1-yl) methyl]-(S)-1-azabicyclo [2.2.2] octane-3-amine to form salt, thus obtaining the palonosetron hydrochloride hydrochloride. The synthesis process provided by the invention is mild in condition, simple in step and high in yield and has advantages superior to the prior art.