208038-01-1

Basic information

• Product Name: (1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one
• CAS NO: 208038-01-1
• Molecular Weight: 215.295
• Mol File: 208038-01-1.mol

Chemical Properties

• CAS DataBase Reference: (1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one(208038-01-1)
• EPA Substance Registry System: (1S,5R)-8-benzyl-8-azabicyclo[3.2.1]octan-2-one(208038-01-1)

Safety Data

• Hazardous Substances Data: 208038-01-1(Hazardous Substances Data)

Upstream product

• 208037-93-8 (S)-dibenzyl 2-(1-benzyl-5-(tert-butoxycarbonyl)pyrrolidin-2-ylidene)succinate 
• 208037-98-3 (1S,5R)-8-Benzyl-2-hydroxy-8-aza-bicyclo[3.2.1]oct-2-ene-3-carboxylic acid methyl ester 

Downstream Products

• 208038-10-2 (1S,2S,3R,5R)-3-Benzoyloxy-2-carbamoyl-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester 
• 208038-11-3 Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 
• 134623-91-9 benzoylecgonine 
• 208038-12-4 Benzoic acid (1S,2S,3R,5R)-2-carbamoyl-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester 
• 47195-07-3 (+)-cocaine 
• 208038-02-2 (1S,5R)-8-(tert-butyloxycarbonyl)-8-azabicyclo[3.2.1]-2-octanone 

Relevant articles and documents

Pyrimidoaminotropanes as potent, selective, and efficacious small molecule kinase inhibitors of the mammalian target of rapamycin (mTOR)

We have recently reported a series of tetrahydroquinazoline (THQ) mTOR inhibitors that produced a clinical candidate 1 (GDC-0349). Through insightful design, we hoped to discover and synthesize a new series of small molecule inhibitors that could attenuate CYP3A4 time-dependent inhibition commonly observed with the THQ scaffold, maintain or improve aqueous solubility and oral absorption, reduce free drug clearance, and selectively increase mTOR potency. Through key in vitro and in vivo studies, we demonstrate that a pyrimidoaminotropane based core was able to address each of these goals. This effort culminated in the discovery of 20 (GNE-555), a highly potent, selective, metabolically stable, and efficacious mTOR inhibitor.

Enantiospecific Synthesis of Natural (-)-Cocaine and Unnatural (+)-Cocaine from D- And L-Glutamic Acid

Natural (-)-cocaine and unnatural (+)-cocaine have been synthesized enantiospecifically from D-and L-glutamic acid, respectively. The axial-equatorial substitutents were introduced by a stereo-and regiospecific dipolar cycloaddition to the corresponding (1R,5S)- and (1S,5R)-N-BOC-nortropenes with (ethoxycarbonyl)formonitrile N-oxide. A sequence of subsequent stereochemically controlled transformations converted the fused isoxazoline to the requisite β-hydroxy ester. Synthesis of the key intermediate N-BOC-nortropenes involved construction of the 8-azabicyclo[3.2.1]octane framework by Dieckmann condensation of cis-5-substituted D- and L-proline esters. For comparison, (1R,5S)-N-BOC-nortropene also was derived by degradation from natural cocaine. The cis-5-substituted D- and L-proline esters were obtained by sulfide contraction and subsequent catalytic hydrogenation to induce stereospecifically the C-5 stereochemistry from D- and L-thiopyroglutamate, which in turn were prepared from D- and L-glutamic acids, respectively.