Synthesis and Resolution of Racemic
 Trans
 ‐2‐(
 <scp>
 N
 </scp>
 ‐Benzyl)Amino‐1‐Cyclohexanol: Enantiomer Separation by Sequential Use of (
 <scp>
 R
 </scp>
 )‐ and (
 <scp>
 S
 </scp>
 )‐Mandelic Acid

Schiffers, Ingo; Bolm, Carsten

doi:10.1002/0471264229.os085.12

Cited by 3 publications

(1 citation statement)

References 28 publications

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“…After a preliminary screen of chiral acids we found that we were able to obtain clean trans -3-aminocyclohexanol mandelate (±)-7 by crystallization of cis -/ trans -3-aminocyclohexanol 6 with (±)-mandelic acid. Resolution of the corresponding trans -2-( N -benzyl)aminocyclohexanol by sequential use of ( R )- and ( S )-mandelic acid was recently reported by Bolm et al , …”

Section: Resultsmentioning

confidence: 87%

Diastereoisomeric Salt Formation and Enzyme-Catalyzed Kinetic Resolution as Complementary Methods for the Chiral Separation of cis-/trans-Enantiomers of 3-Aminocyclohexanol

Brocklehurst

Laumen

Vecchia

et al. 2010

Org. Process Res. Dev.

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This contribution demonstrates the preparative-scale synthesis of (1S,3S)-3-aminocyclohexanol by either enzymatic kinetic resolution of Cbz-protected 3-aminocyclohexanols or direct diastereoisomeric salt formation with (R)-mandelic acid. The salt formation demonstrates how a single enantiomer, (1S,3S)-3-aminocyclohexanol (R)-mandelate, can be effectively isolated from the cis/trans racemic mixture and subsequently converted to the free amine, (1S,3S)-3-aminocyclohexanol, by ion-exchange chromatography. We have also demonstrated how the other three enantiomers of 3-aminocyclohexanol can be prepared by either diastereoisomeric salt formation or enzymatic kinetic resolution.

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Section: Resultsmentioning

confidence: 87%

Diastereoisomeric Salt Formation and Enzyme-Catalyzed Kinetic Resolution as Complementary Methods for the Chiral Separation of cis-/trans-Enantiomers of 3-Aminocyclohexanol

Brocklehurst

Laumen

Vecchia

et al. 2010

Org. Process Res. Dev.

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High throughput solid-phase screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols

et al. 2020

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An Improved and Efficient Process for the Scalable Preparation of Optically Pure Trans-2-Aminocyclohexanols

Xue

Zhu

et al. 2014

Journal of Chemical Research

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An improved and efficient process has been developed for a green and scalable preparation of optically pure (1R,2R)-and (1S,2S)-trans-2-aminocyclohexanols. The process utilised hot water to promote the aminolysis of cyclohexene oxide by benzylamine to afford racemic trans-2-(benzylamino)cyclohexanols, which were resolved by sequential and repeated use of (R)-and (S)-mandelic acid. Finally, after treatment of the two salts sequentially with HCl and NaOH and recovery of mandelic acid, liberation was achieved of the optically pure trans-2-benzylaminoaminocyclohexanols which were smoothly debenzylated using a low loading of a Pd/C catalyst to the trans-2-aminocyclohexanols. The synthetic route has been successfully applied to large-scale (1 mol) preparations in good yield.

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Synthesis and Resolution of Racemic Trans ‐2‐( N ‐Benzyl)Amino‐1‐Cyclohexanol: Enantiomer Separation by Sequential Use of ( R )‐ and ( S )‐Mandelic Acid

Abstract: Cyclohexene oxide Benzylamine ( S )‐(+)‐Mandelic acid ( R )‐(−)‐Mandelic acid ( S )‐Mandelic salt of (1 R … Show more

Cited by 3 publications

References 28 publications

Diastereoisomeric Salt Formation and Enzyme-Catalyzed Kinetic Resolution as Complementary Methods for the Chiral Separation of cis-/trans-Enantiomers of 3-Aminocyclohexanol

Diastereoisomeric Salt Formation and Enzyme-Catalyzed Kinetic Resolution as Complementary Methods for the Chiral Separation of cis-/trans-Enantiomers of 3-Aminocyclohexanol

High throughput solid-phase screening of bacteria with cyclic amino alcohol deamination activity for enantioselective synthesis of chiral cyclic β-amino alcohols

An Improved and Efficient Process for the Scalable Preparation of Optically Pure Trans-2-Aminocyclohexanols

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