Synthesis of 2-Alkylaminoethanols from Ethanolamine

Cope, Arthur C.; Hancock, Evelyn M.

doi:10.1021/ja01259a005

Cited by 46 publications

(16 citation statements)

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“…[73] PtO 2 has found very little application in reductive amination processes because of the difficulties to reduce it prior to contacting the substrates. [74] Sulphided platinum metal catalysts have given excellent results because of their particular resistance to poisoning and their ability to minimise reduction of the carbonyl to an alcohol, even if sometimes this is to the detriment of displaying a lower activity. [21,75] Fe and Cu have also been used in the hydrogenation of nitriles, but much less often than the above-mentioned metals because they are considered to be less active.…”

Section: Effect Of the Catalystmentioning

confidence: 99%

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

Gomez

Peters

Maschmeyer

2002

Advanced Synthesis & Catalysis

514

238

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This review deals with two of the most commonly used methods for the preparation of amines: the reductive amination of aldehydes and ketones and the hydrogenation of nitriles. There is a great similarity between these two methods, since both have the imine as intermediate. However, due to the high reactivity of this intermediate, primary, secondary and/or tertiary amines are obtained (often simultaneously). The relation of the selectivity to different substrate structures and reaction conditions is briefly summarised, the main focus being on the catalyst as it is the most significant factor that governs the selectivity. Different mechanisms are discussed with the view to correlate the structure of the catalyst and, more particularly, the nature of the metal and the support with selectivity. The crucial point is the presumed location of the condensation and hydrogenation steps.

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Section: Effect Of the Catalystmentioning

confidence: 99%

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

Gomez

Peters

Maschmeyer

2002

Advanced Synthesis & Catalysis

514

238

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“…Chiral intermediates (R)-4 and (S)-5 were successfully condensed with ketone (cyclohexanone or acetone) to afford chiral oxazolidine without any catalyst. The possible mechanism of this reaction is depicted in Scheme . The first step of this reaction was the nucleophilic addition of amino and the carbonyl to form an aminodiol.…”

Section: Resultsmentioning

confidence: 99%

A Mild and Highly Efficient Synthesis of Chiral N‐Dichloroacetyl‐4‐ethyl‐1,3‐oxazolidines

Zhao

et al. 2012

Journal of Heterocyclic Chem

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Chiral 2‐amino‐butanols (4 and 5) were obtained via the isolation of diastereomeric salt. Then, chiral compounds (6–9) were synthesized by a sequential procedure involving condensation of chiral 2‐amino‐butanol with ketone and dichloroacetyl chloride. All the compounds were characterized by IR, 1H NMR, 13C NMR, and element analysis. The absolute configurations of (S)‐8 was determined by X‐ray crystallography.

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“…It has been reported that condensation of ketones with ethanolamine can lead to alkylidene amino alcohols or oxazolidines 19 . However, cyclohexanone and ethanolamine yield cyclohexane spiro-2'-(r,3'-oxazolidine) 20 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis And Biological Evaluation Of Some New Alicyclicspiro-2'-(1',3'-Oxazolidine) Derivatives

Faidallah¹,

Sharshira²,

Al-Saadi³

2009

Heterocyclic Communications

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Condensation of cyclic ketones J. with ethänolamines gave the corresponding spiro-oxazolidines 2. The thioamides 3 were obtained in good yields through reaction of 2 with the appropriate isothiocyanate. Reaction of 2 with formaldehyde or acetaldehyde in the presence of the appropriate amine afforded the corresponding aminomethyl spiro-compounds 4 and 5 respectively, in excellent yields. The structures of the isolated compounds were fully determined by spectral methods. Antimicrobial activities of some oxazolidines were also discussed.

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Synthesis of 2-Alkylaminoethanols from Ethanolamine

Cited by 46 publications

References 0 publications

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

A Mild and Highly Efficient Synthesis of Chiral N‐Dichloroacetyl‐4‐ethyl‐1,3‐oxazolidines

Synthesis And Biological Evaluation Of Some New Alicyclicspiro-2'-(1',3'-Oxazolidine) Derivatives

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