188624-92-2

Upstream product

• 50910-54-8 trans-4-aminocyclohexanol hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 27514-07-4 7-azabicyclo[2.2.1]heptane hydrochloride 
• 343313-51-9 N-(trans-4-hydroxycyclohexyl)-4-methylbenzenesulfonamide 

Downstream Products

• 863561-73-3 C₃₁H₄₆N₄O 
• 863561-58-4 3-[3,3-dimethyl-4-oxo-4-(7-azabicyclo[2.2.1]heptan-7-yl)butyl]-4-[(1S)-1-methyl-2-{1-benzyl-pyrrolidin-3-ylamino}ethyl]-5-(3,5-dimethylphenyl)-1H-pyrrole 
• 863561-74-4 C₃₈H₄₈N₄OS 
• 863561-51-7 3-[3,3-dimethyl-4-oxo-4-(7-azabicyclo[2.2.1]heptan-7-yl)butyl]-4-[2-{4-(morpholin-4-ylcarbonyl)piperidin-1-yl}ethyl]-5-(3,5-dimethylphenyl)-1H-pyrrole 
• 27514-07-4 7-azabicyclo[2.2.1]heptane hydrochloride 

Relevant academic research and scientific papers

Synthesis of N-heteroaryl-7-azabicyclo[2.2.1]heptane derivatives via palladium-bisimidazol-2-ylidene complex catalyzed amination reactions

(equation presented) A one-step approach to novel N-heteroaryl-substituted-7-azabicyclo[2.2.1]heptanes from readily available heteroaryl halides and 7-azabicyclo-[2.2.1]heptane has been achieved. The cross-coupling amination reaction employs palladium-bis

Fischer synthesis of isomeric thienopyrrole LHRH antagonists

As part of a structure-activity exploration into LHRH antagonists, structures containing the thieno[2,3-b]pyrrole core were identified as potent antagonists. This letter describes the employment of the Fischer synthesis to access this thienopyrrole and isomeric final compounds.

PYRROLE DERIVATIVES AS GONADOTROPIN RELEASING HORMONE (GNRH) ANTAGONISTS

The invention relates to a group of novel thieno-pyrrole compounds of formula (I) wherein: R1,R2, R3, R4 M, and R5 are as defined in the specification, as inter alia, gonadotrophin releasing hor

THIENOPYROLES AS ANTAGONISTS OF GNRH

The invention relates to a group of novel thieno-pyrrole compounds of Formula (I) wherein: R1, R2, R3, R4 and R5 are as defined in the specification, which are useful as gonadotrophin releasing hormon

Microbiological Oxygenation of Bridgehead Azabicycloalkanes

A series of N-substituted bridgehead azabicycloalkanes has been prepared and examined as substrates for microbiological oxygenation using the fungi Beauveria bassiana, Rhizopus nigricans, Aspergillus ochraceus, and Rhizopus arrhizus. Oxygenation using B. bassiana of N-tosyl-7- azabicyclo[2.2.1]heptane gave N-[p-(hydroxymethyl)benzenesulfonyl]-7-azabicyclo[2.2.1]heptane (56% yield), of N-(phenyloxycarbonyl)-7-azabicyclo[2.2.1]heptane gave the 2-endo-ol (56% yield, 51% ee), of N-BOC-7-azabicyclo[2.2.1]heptane gave the 2-endo-ol (10% yield), of N-Cbz-7-azabicyclo- [2.2.1]heptane gave the 2-endo-ol (28%), of N-(phenyloxycarbonyl)-8-azabicyclo[3.2.1]octane gave the 3-endo-ol, and of N-(phenyloxycarbonyl)-9-azabicyclo[3.3.1]nonane gave the 3-exo-ol (30%) and 3-one (16%). Oxygenation using R. nigricans of N-BOC-7-azabicyclo[2.2.1]heptane gave the 2-endo-ol (62% yield, 28% ee) and the 2-exo-ol (27% yield, 42% ee). Oxidation of the N-BOC-7-azabicyclo- [2.2.1]heptan-2-ols gives the 2-ketone, a synthetic intermediate useful for conversion to the natural product, epibatidine. Oxygenation of N-(phenyloxycarbonyl)-7-azabicyclo[2.2.1]heptane using R. arrhizus gives the 2-endo-ol (5% yield, 31% ee) and the 2-exo-ol (18% yield, 22% ee). Oxygenation of N-(phenyloxycarbonyl)-8-azabicyclo[3.2.1]octane using A. ochraceous gives the 3-endo-ol (36%) and the 3-one (4%).