95687-85-7

Upstream product

• 529-17-9 tropane 
• 65-85-0 benzoic acid 
• 155394-39-1 1-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidine 
• 98-88-4 benzoyl chloride 
• 95205-45-1 5-{(3aR,5S,6S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid 
• 95687-90-4 N-((1S,4R)-4-Hydroxy-cyclohept-2-enyl)-benzamide 
• 95687-91-5 N-((1S,4R)-4-Hydroxy-cycloheptyl)-benzamide 
• 182343-68-6 (2-Iodo-phenyl)-[2-(3-trimethylsilanyl-prop-2-ynyl)-piperidin-1-yl]-methanone 
• 182343-67-5 tert-butyl 2-(3-trimethylsilyl-2-propynyl)piperidine-1-carboxylate 
• 182343-66-4 2-(3,3-dibromo-2-propenyl)-1-piperidinecarboxylic acid tert-butyl ester 
• 170491-61-9 2-(2-oxoethyl)-1-piperidinecarboxylic acid tert-butyl ester 
• 118811-03-3 tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate 
• 609-67-6 2-Iodobenzoyl chloride 
• 1484-84-0 2(RS)-(2-hydroxyethyl)piperidine 

Downstream Products

• 18717-73-2 (1R,3r,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-3-ol 

Relevant academic research and scientific papers

Catalyst-Controlled Diastereoselective Synthesis of Cyclic Amines via C-H Functionalization

Reliable regio- and stereochemical techniques applicable to nonactivated aliphatic systems remain largely elusive due to the challenges of discriminating between multiple, relatively strong sp3 C-H bonds whose chemical behavior often differ onl

Synthesis of bridged azabicyclic compounds using radical translocation reactions of 1-(o-halogenobenzoyl)-2-(prop-2-enyl)-and -(prop-2-ynyl)-piperidines

Methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)piperidine-2-carboxylate 8a, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave regioselectively the 8-azabicyclo[3.2.1]octane 14a (a 5-exo cyclisation product) in quantitative yield as a diastereomeric mixture (66:34). 1-(o-Bromobenzoyl)-2-(prop-2-enyl)piperidine 13 also gave the 8-azabicyclo-[3.2.1]octane 16 (75% as a diastereomeric mixture), along with the pyrido[2,1-a]isoindolone 17 (10%) and the simple reduction product 18 (5%). 1-(o-Iodobenzoyl)-2-[3-(trimethylsilyl)prop-2-ynyl]piperidine 23 afforded, in addition to the pyrido[2,1-a]isoindolone 25 (18%), the 8-azabicyclo-[3.2.1]octane 24 (75%) which was converted into the 6-oxo derivative 27. For comparison, the behaviour of the azetidine congener 31 was also examined.

Synthesis of bridged azabicyclic compounds using raducal translocation reactions of 1-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidines

A new synthesis of the 7-azabicycloheptane and 8-azabicyclooctane systems is described in which α-acylamino radicals generated from 1-(o-bromobenzoyl-2-(prop-2-enyl)pyrrolidines by a Bu3SnH-mediated radical translocation reaction are cyclised.Treatment of methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidine-2-carboxylate 3a with Bu3SnH in the presence of a catalytic amount of azoisobutyronitrile in boiling toluene gave the 7-azabicycloheptane 4a (a 5-exo cyclisation product) and the 8-azabicyclooctane 5a (a 6-endo product) (30percent), together with the reduction product 6a (12percent).The geriochemistry (5-exo/6-endo) of this cyclisation could be controlled by the introduction of a substituent on the prop-2-enyl group.The substituent(s) at the 2- and/or 4-position(s) of the pyrrolidine ring were found to play an important role in this cyclisation.

SYNTHESIS OF 7-AZABICYCLOHEPTANE AND 8-AZABICYCLOOCTANE SYSTEMS USING RADICAL CYCLIZATION

A new method for the synthesis of the titled systems using cyclization of the α-acylamino radicals generated from methyl N-(o-bromobenzoyl)-2-(prop-2-enyl)pyrrolidine-2-carboxylates and the piperidine congener by Bu3SnH-mediated radical translocation reaction is described.

A NEW SYNTHETIC ROUTE TO TROPANE ALKALOIDS. PSEUDOTROPINE AND TROPACOCAINE

Pseudotropine and tropacocaine have been synthesized by a facile route involving the nitroso cycloaddition followed by internal SN2 displacement.