29900-93-4

Basic information

• Product Name: [1R-(2-endo,3-exo)]-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• Synonyms: (1R-(2-endo,3-exo))-3-Amino-1,7,7-trimethylbicyclo(2.2.1)heptan-2-ol; 3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS NO: 29900-93-4
• Molecular Formula: C₁₀H₁₉NO
• Molecular Weight: 169.264
• EINECS: 249-941-0
• Mol File: 29900-93-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 237.5°C at 760 mmHg
• Flash Point: 97.4°C
• Density: 1.038g/cm³
• Vapor Pressure: 0.00797mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: [1R-(2-endo,3-exo)]-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: [1R-(2-endo,3-exo)]-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol(29900-93-4)
• EPA Substance Registry System: [1R-(2-endo,3-exo)]-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol(29900-93-4)

Safety Data

• Hazardous Substances Data: 29900-93-4(Hazardous Substances Data)

Usage

General Description

The chemical [1R-(2-endo,3-exo)]-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol is a bicyclic compound with a tertiary amine and a hydroxyl functional group. It has a molecular formula of C11H21NO and a molecular weight of 183.29 g/mol. [1R-(2-endo,3-exo)]-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol is a chiral molecule with a stereocenter at the first carbon atom. It can be used in organic synthesis as a building block for the preparation of various pharmaceuticals and agrochemicals. Additionally, it may have potential applications in medicinal chemistry and drug discovery due to its unique bicyclic structure and functional groups.

Upstream product

• 2438-17-7 3-amino-bornan-2-one 
• 663-17-2 (1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 60-29-7 diethyl ether 
• 33162-63-9 3-endo-aminobornan-2-one 
• 31638-54-7 (1R,3S,4S)-(+)-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one hydrochloride 
• 31571-14-9 (1R,E)-(+)-camphorquinone 3-oxime 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 151288-80-1 (1R,2R,3S,4S)-3-benzoylamino-2-benzoyloxy-1,7,7-trimethylbicyclo<2.2.1>heptane 
• 10334-26-6 (R)-camphorquinone 
• 41719-63-5 (1R,2R,6S,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0(2,6)]decan-4-one 
• 136009-18-2 N-<(1R,2R,3S,4S)-2-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-3-yl>-benzamide 
• 162425-97-0 (1R,2S,4S)-2-exo-hydroxy-3-(hydroxyimino)-1,7,7-trimethylbicyclo<2.2.1>heptane 

Downstream Products

• 127393-14-0 N-<(1R,2R,3S,4S)-2-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-3-yl>-2<(S)-1-benzyloxycarbonyl>prolinamide 
• 144397-14-8 Benzyl-((1S,2S,6R)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-ylmethyl)-amine 
• 107244-02-0 Cyclohexylidene-((1S,2S,3R,4R)-3-methoxy-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine 
• 211869-55-5 (1R,2R,6S,7S)-4-Allyl-1,10,10-trimethyl-5-(toluene-4-sulfonyl)-3-oxa-5-aza-4-bora-tricyclo[5.2.1.0^2,6]decane 
• 131343-28-7 (1R,2R,3S,4S)-3-benzylamino-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol 
• 193340-27-1 (1R,2R,3S,4S)-3-(4-vinylbenzenesulfonyl)amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 
• 40724-51-4 C₁₉H₂₆N₂O₆S 
• 144397-23-9 (1S,2S,6R)-1,10,10-Trimethyl-4-phenylselanylmethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 

Relevant articles and documents

Asymmetric reduction of α-keto aldoxime o -ethers

The catalytic asymmetric reduction of -keto aldoxime O-methyl, O-benzyl, and O-trityl ethers, derived from substituted acetophenones, with borane/oxazaborolidines, by transfer hydrogenation, and with yeast, was studied. The reduction with borane/oxazaborolidines produced the corresponding -hydroxy oxime ethers, -hydroxy hydroxylamine ethers, and -amino alcohols in 39-78% yields and up to 77% ee. The carbonyl group was selectively reduced by transfer hydrogenation with formic acid-triethylamine catalyzed by RhCl[(R,R)-TsDPEN](Ce, and also with yeast, producing -hydroxy oxime ethers, up to 75% ee and 93% ee, respectively. Georg Thieme Verlag Stuttgart New York.

The practical synthesis of a uterine relaxant, Bis( 2-{[(2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl) -phenyl]ethyl}amino) -1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246)

The synthetic route for a uterine relaxant, bis(2-{[ (2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3- (2-hydroxyethyl)-phenyl]ethyl}amino) -1,2,3,4-tetrahydronaphthalen-7-y1]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now describe the practical synthesis of these two optically active components. Bromohydrin 14 was obtained by the asymmetric borane reduction of the prochiral phenacyl bromide 13 using a catalyst prepared from aluminum triethoxide and a chiral amino alcohol. The other optically active component 24 was prepared from (S)-AMT.

Preparative scale synthesis of (+) endo-2-hydroxy-endo-3-aminobornane

A convenient preparation of the enantiomerically pure title compound is proposed from (+) camphor in 5 steps with an overall yield between 42 and 62percent.The benzoylation of this compound leads to the expected products 6 and 8 and to the oxazoline 10 formed from 6 with retention of configuration.Key Words: chiral 2-hydroxy-3-aminobornanes / benzoylation / acidic hydrolysis