152533-46-5

Basic information

• Product Name: (1r,2r,4s)-rel-7-boc-7-azabicyclo[2.2.1]heptan-2-ol
• Synonyms: (1r,2r,4s)-rel-7-boc-7-azabicyclo[2.2.1]heptan-2-ol;(1R,2R,4S)-rel-tert-Butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate
• CAS NO: 152533-46-5
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.28
• Mol File: 152533-46-5.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 310.3±25.0 °C(Predicted)
• Appearance: /
• Density: 1.181±0.06 g/cm3(Predicted)
• PKA: 14.72±0.20(Predicted)
• CAS DataBase Reference: (1r,2r,4s)-rel-7-boc-7-azabicyclo[2.2.1]heptan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1r,2r,4s)-rel-7-boc-7-azabicyclo[2.2.1]heptan-2-ol(152533-46-5)
• EPA Substance Registry System: (1r,2r,4s)-rel-7-boc-7-azabicyclo[2.2.1]heptan-2-ol(152533-46-5)

Safety Data

• Hazardous Substances Data: 152533-46-5(Hazardous Substances Data)

Usage

Description

(1r,2r,4s)-rel-7-boc-7-azabicyclo[2.2.1]heptan-2-ol is a bicyclic organic compound that is a white crystalline solid with a molecular formula of C13H23NO3. It has a seven-membered ring containing a nitrogen atom and a Boc group on the amine functionality. The stereochemistry (1r,2r,4s) refers to the specific arrangement of atoms in space, which is important in determining its biological activity and reactivity in chemical reactions.

Uses

Used in Organic Synthesis:
(1r,2r,4s)-rel-7-boc-7-azabicyclo[2.2.1]heptan-2-ol is used as a building block in the synthesis of various organic compounds and pharmaceuticals. The Boc group on the amine functionality can be removed using acidic or basic conditions, making it a versatile intermediate in organic synthesis.
Used in Pharmaceutical Industry:
(1r,2r,4s)-rel-7-boc-7-azabicyclo[2.2.1]heptan-2-ol is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique bicyclic structure and stereochemistry. Its specific arrangement of atoms in space allows for the development of drugs with targeted biological activity.

Upstream product

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

Downstream Products

• 163513-98-2 (-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 152533-47-6 (exo)-7-(1,1-dimethylethoxycarbonyl)-7-azabicyclo[2.2.1]heptan-2-one 
• 152614-12-5 tert-butyl (1R,2R,4S)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 152533-46-5 7-<(1,1-dimethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-endo-ol 
• 152885-09-1 (+)-epibatidine hydrochloride 
• 152885-09-1 (-)-epibatidine hydrochloride 
• 140111-52-0 epibatidine 
• 163513-99-3 (1S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo<2.2.1>heptan-2-one 
• 152378-30-8 (-)-epibatidine 
• 152533-46-5 (2-endo)-2-hydroxy-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 154905-39-2 (-)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol 
• 154905-38-1 (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol 
• 163513-98-2 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 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 

Relevant articles and documents

Enantioselective approach to 7-azabicyclo[2.21lheptane ring systems using D-(-)quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine

By utilizing, D-(-)-quinic acid as the chiral starting material the optically pure 7-[(1,1-dimethylethoxy)carbonyl]-7-azabicyclo[ 2.2.1]heptan-2-one 2, an advanced intermediate already taken to (+)-epibatidine 1, a non-opioid analgesic isolated from Ecuadorian poison frogs, was synthetized through a facile, regioselective intramolecular nucleophilic ring opening of a cyclic sulfate moiety.

Substituted Azabicyclo[2.2.1]heptanes as Selective Orexin-1 Antagonists: Discovery of JNJ-54717793

The orexin system consists of two neuropeptides (orexin-A and orexin-B) that exert their mode of action on two receptors (orexin-1 and orexin-2). While the role of the orexin-2 receptor is established as an important modulator of sleep wake states, the role of the orexin-1 receptor is believed to play a role in addiction, panic, or anxiety. In this manuscript, we describe the optimization of a nonselective substituted azabicyclo[2.2.1]heptane dual orexin receptor antagonist (DORA) into orally bioavailable, brain penetrating, selective orexin-1 receptor (OX1R) antagonists. This resulted in the discovery of our first candidate for clinical development, JNJ-54717793.

Substituted Imidazopyridines as HDM2 Inhibitors

The present invention provides substituted imidazopyridines as described herein or a pharmaceutically acceptable salt or solvate thereof. The representative compounds are useful as inhibitors of the HDM2 protein. Also disclosed are pharmaceutical compositions comprising the above compounds and potential methods of treating cancer using the same.