152614-12-5

Basic information

• Product Name: tert-butyl (1R,2R,4S)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate
• CAS NO: 152614-12-5
• Molecular Weight: 213.277
• Mol File: 152614-12-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: tert-butyl (1R,2R,4S)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (1R,2R,4S)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate(152614-12-5)
• EPA Substance Registry System: tert-butyl (1R,2R,4S)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate(152614-12-5)

Safety Data

• Hazardous Substances Data: 152614-12-5(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 191468-74-3 2-endo-hydroxy-7-azanorbornane 
• 191468-74-3 (1S,2S,4R)-7-Aza-bicyclo[2.2.1]heptan-2-ol 
• 152533-47-6 (exo)-7-(1,1-dimethylethoxycarbonyl)-7-azabicyclo[2.2.1]heptan-2-one 
• 163513-98-2 (-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 152533-46-5 (2-endo)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 187160-29-8 Methanesulfonic acid (3aR,5R,7aS)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester 
• 200340-46-1 Methanesulfonic acid (3aR,5S,7aS)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester 
• 187160-32-3 (3aR,5S,7aS)-5-Azido-hexahydro-benzo[1,3,2]dioxathiole 2,2-dioxide 
• 187160-30-1 (3aR,5S,7aS)-5-Azido-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 187160-33-4 Sulfuric acid mono-(1R,2R,4S)-(7-aza-bicyclo[2.2.1]hept-2-yl) ester 
• 187160-31-2 (1S,3R,4S)-1-azido-3,4-dihydroxy-cyclohexane 
• 121573-17-9 (3aR,7aS)-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 188624-94-4 7-tert-butoxycarbonyl-7-azabicyclo<2.2.1>heptane 

Downstream Products

• 163513-98-2 (-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate 

Relevant articles and documents

The Synthesis of (+)- and (-)-Epibatidine

The synthesis of the alkaloid epibatidine heptane> in enantiomeric form involving, as the critical step, reaction or 5-lithio-2-chloropyridine with N-tert-butoxycarbonyl-7-azabicycloheptan-2-one is des

7-AZONIABICYCLO [2.2.1] HEPTANE DERIVATIVES, METHODS OF PRODUCTION, AND PHARMACEUTICAL USES THEREOF

Muscarinic acetylcholine receptor antagonists and methods of using them for the treatment of muscarinic acetylcholine receptor-mediated diseases, such as pulmonary diseases, are provided.

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%).