41719-73-7

Basic information

• Product Name: 1R)-3-endo-Aminoborneol
• Synonyms: 1R)-3-endo-Aminoborneol
• CAS NO: 41719-73-7
• Molecular Formula: C₁₀H₁₉NO
• Molecular Weight: 169.26396
• Mol File: 41719-73-7.mol

Chemical Properties

• Appearance: /
• Solubility: DCM, Methanol
• CAS DataBase Reference: 1R)-3-endo-Aminoborneol(CAS DataBase Reference)
• NIST Chemistry Reference: 1R)-3-endo-Aminoborneol(41719-73-7)
• EPA Substance Registry System: 1R)-3-endo-Aminoborneol(41719-73-7)

Safety Data

• Hazardous Substances Data: 41719-73-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1R)-3-endo-Aminoborneol is used as a key intermediate in the synthesis of Gibornuride (G409700), an anti-diabetic drug belonging to the sulfonylurea class. 1R)-3-endo-Aminoborneol plays a crucial role in the development of medications aimed at managing blood sugar levels in patients with diabetes.
In the synthesis of Gibornuride, (1R)-3-endo-Aminoborneol serves as a precursor, enabling the formation of the final drug product through a series of chemical reactions. Its unique structural features and reactivity make it an essential component in the production process, contributing to the effectiveness of the resulting anti-diabetic medication.

Upstream product

• 33162-63-9 3-endo-aminobornan-2-one 
• 162425-97-0 (1R,2S,4S)-2-exo-hydroxy-3-(hydroxyimino)-1,7,7-trimethylbicyclo<2.2.1>heptane 
• 663-17-2 (1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 

Downstream Products

• 116407-55-7 N-<(1R,2S,3R,4S)-2-hydroxy-1,7,7-trimethylbucyclohept-3-yl>-3-(phenylthio)-2-<(phenylthio)methyl>propanamide 
• 136085-88-6 N-<(1R,2S,3R,4S)-2-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-3-yl>-2-<(S)-1-benzyloxycarbonyl>prolinamide 
• 103729-96-0 (-)-3-exo-(Dimethylamino)isoborneol 
• 193340-25-9 (1R,2S,3R,4S)-3-(4-vinylbenzenesulfonyl)amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 
• 135969-12-9 (1R,2S,3R,4S)-3-benzylamino-1,77-trimethylbicyclo<2.2.1>heptan-2-ol 
• 1355359-50-0 C₁₇H₂₇NO₂ 
• 1355359-45-3 C₃₁H₃₉NO₄ 
• 1355359-59-9 C₃₃H₄₃NO₇ 
• 1355359-53-3 C₁₇H₂₅NO 
• 144397-21-7 4-Methyl-N-((1S,2S,6R)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-en-4-ylmethyl)-benzenesulfonamide 
• 107196-56-5 cis, exo-3-cyclohexylideneamino-2-methoxybornane 

Relevant articles and documents

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.

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.

Stereoselective Reactions. XI. Asymmetric Alkylation of Cyclohexanone via Chiral Chelated Lithioenamines Derived from D-Camphor Derivatives

Metalation and alkylation of the chiral imines prepared from cyclohexanone and methoxy amines (2b, 4c, 6d and 7d) derived from D-camphor derivatives provided, after hydrolysis, optically active 2-alkylcyclohexanones (9) in high enantiomeric purities of up to 99.5percent.Keywords - asymmetric synthesis; asymmetric alkylation; D-camphor; chiral methoxy amine; 2-alkylcyclohexanone; chelated lithioenamine.