154905-38-1

Basic information

• Product Name: (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol
• CAS NO: 154905-38-1
• Molecular Weight: 213.277
• Mol File: 154905-38-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol(154905-38-1)
• EPA Substance Registry System: (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol(154905-38-1)

Safety Data

• Hazardous Substances Data: 154905-38-1(Hazardous Substances Data)

Upstream product

• 163513-99-3 (1S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo<2.2.1>heptan-2-one 
• 1319725-09-1 (1S,4'R,5'R)-tert-butyl 4',5'-diphenyl-7-azaspiro[bicyclo[2.2.1]heptane-2,2'-imidazolidine]-7-carboxylate 
• 163513-98-2 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 191468-74-3 7-azabicyclo[2.2.1]heptan-2-ol 
• 510748-36-4 tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 152533-46-5 (±)-tert-butyl-(1SR,2RS,4RS)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 152533-42-1 N-Benzyl-N-cyclohex-3-enyl-2,2,2-trifluoro-acetamide 
• 78293-47-7 N-<(Trifluoroacetyl)amino>cyclohex-3-ene 
• 24424-99-5 di-tert-butyl dicarbonate 
• 188624-94-4 7-tert-butoxycarbonyl-7-azabicyclo<2.2.1>heptane 
• 154905-37-0 (1S,2R,4R)-2-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 

Downstream Products

• 152378-30-8 (-)-epibatidine 
• 163513-99-3 (1S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo<2.2.1>heptan-2-one 

Relevant articles and documents

Total Synthesis and Determination of the Absolute Configuration of Epibatidine

The synthesis of (+)- and (-)-epibatidine (exo-2-(2-chloropyridin-5-yl)-7-azabicycloheptane) via reaction of 5-lithio-2-chloropyridine with (+)- and (-)-N-BOC-7-azabicycloheptan-2-one is described.The absolute configuration of the natural product is shown to be 1R,2R,4S.

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%).