174293-29-9

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 931-15-7 (1S,2S)-trans-2-aminocyclohexanol 
• 123-75-1 pyrrolidine 
• 286-20-4 cyclohexane-1,2-epoxide 
• 322407-34-1 (1S,2S)-trans-2-(N-benzyl)amino-1-cyclohexanol 
• 108-05-4 vinyl acetate 
• 69420-67-3 (+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol 

Downstream Products

• 222401-10-7 6-Methoxy-2-(4-methoxyphenyl)-3-(4-[2-pyrrolidin-1-ylcyclohexoxy]benzoyl)benzo[b]thiophene 

Relevant academic research and scientific papers

Highly regioselective ring-opening of epoxides with amines: A metal- A nd solvent-free protocol for the synthesis of β-amino alcohols

We herein report a metal- A nd solvent-free acetic acid-mediated ring-opening reaction of epoxides with amines. This process provides β-amino alcohols in high yields with excellent regioselectivity. Importantly, this epoxide ring-opening protocol can be used for the introduction of amines in natural products during late-stage transformations.

Fe(Cp)2BF4: An efficient lewis acid catalyst for the aminolysis of epoxides

Ferrocenium tetrafluoroborate [Fe(Cp)2BF4] is an efficient Lewis acid catalyst for the aminolysis of aromatic, aliphatic, and cyclic epoxides using aniline and substituted anilines as the nucleophile to provide regioselective β-amino alcohols in 61-97% yields under solvent-free conditions at room temperature. The ring opening of cyclohexene oxide with aliphatic amines gave 2-aminocyclohexanols in 33-98% yields at 60 °C under solvent-free conditions. Georg Thieme Verlag Stuttgart New York.

Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis

A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with >99% enantiomeric excess (ee) by sequential use of (R)- and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.

Chemoenzymatic preparation of optically active β-amino-cyclohexanols and their application in the enantioselective addition of diethylzinc to benzaldehyde

Optically active vesamicol and other trans-2-(N,N-dialkylamino) cyclohexanols have been easily prepared in a two step sequence: opening of the oxirane ring of cyclohexene oxide with a secondary amine and subsequent resolution of the resulting racemic amin

New methods of resolution and purification of racemic and diastereomeric amino alcohol derivatives using boric acid and chiral 1,1′-bi-2-naphthol

Resolution of the racemic amino alcohol derivatives 1-6 is readily achieved to obtain enantiomerically enriched compounds using chiral 1,1′-bi-2-naphthol and boric acid in solvents such as CH3-CN, THF, and MeOH. Purification of the diastereomer