Reductive amination using a combination of CaH<sub>2</sub> and noble metal

Guyon, Carole; Silva, Éric Da; Lafon, Romain; Métay, Estelle; Lemaire, Marc

doi:10.1039/c4ra14808h

Cited by 13 publications

(5 citation statements)

References 118 publications

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“…13 C NMR (101 MHz, CDCl 3 ) δ 140.5, 128.3, 128.0, 126.7, 54.0, 49.5, 31.7, 30.0, 27.0, 22.5, 14.0. The compound characterization is in accordance with previous reports [ 49 ].…”

Section: Methodssupporting

confidence: 87%

Titanium-Mediated Reduction of Carboxamides to Amines with Borane–Ammonia

2023

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In this study, the successful titanium tetrachloride-catalyzed reduction of aldehydes, ketones, carboxylic acids, and nitriles with borane–ammonia was extended to the reduction (deoxygenation) of a variety of aromatic and aliphatic pri-, sec- and tert-carboxamides, by changing the stoichiometry of the catalyst and reductant. The corresponding amines were isolated in good to excellent yields, following a simple acid–base workup.

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“…13 C NMR (101 MHz, CDCl 3 ) δ 140.5, 128.3, 128.0, 126.7, 54.0, 49.5, 31.7, 30.0, 27.0, 22.5, 14.0. The compound characterization is in accordance with previous reports [ 49 ].…”

Section: Methodssupporting

confidence: 87%

Titanium-Mediated Reduction of Carboxamides to Amines with Borane–Ammonia

2023

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“…The aldehyde signal is considered the second marker indicating for DA cycloaddition adduct 2b, this signal represents for the only aldehyde proton in the expected structure 2b and appeared as a doublet at δ 9.45 ppm with a coupling constant J 0.8 Hz as well as 13 C-NMR con rms the existence of aldehyde group (CHO) as a single peak at δ 202.73 ppm Reductive amination of the aldehyde 2 using a combination of a commercially available solution of methylamine in methanol, molecular hydrogen and Pd-C afforded the target amine 1. Generally, the two commonly used reductive amination protocols are based on either catalytic hydrogenation or hydride reducing agents; in contrast to hydride reducing agents, the use of molecular hydrogen is economically attractive [19][20][21][22][23][24]. The 1 H and 13 C NMR analysis of the target amine 1 is similar to its precursor 2 with slight differences but the signal of CHO disappeared in amine 1 and IR supported this nding (Fig.…”

Section: Results and Discussion Retrosynthetic Analysis And Strategy For Chlorinated Maprotiline Analoguementioning

confidence: 66%

1,5-Dichloroethanoanthracene Derivatives as Antidepressant Maprotiline Analogues: Synthesis and DFT Computational Calculations

Sultan¹,

Pillai²,

Alzahrani³

2021

Preprint

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The chlorinated tetracyclic 1,5-dichloro-9,10-dihydro-9,10-ethanoanthracen-12-yl)-N-methylmethanamine 1, a maprotiline analogue, has been synthesized via reduction and Diels–Alder reaction followed by reductive amination of Aldehyde 2. Density Functional Theory calculations were performed to identify the possible isomers of the intermediate compound aldehyde 2, these calculations were in a good agreement with experimental result where aldehyde 2 could exist in three isomers with comparable energies. In addition, the side chain of this aldehyde 2 was extended via Wittig reaction to obtain the unsaturated ester 5 that subjected to selective olefinic catalytic hydrogenation to obtain the corresponding saturated ester 6. 1D-NMR (DEPT) and 2D-NMR (HSQC, DQF-COSY) techniques were recruited for structural elucidation in addition to HRMS.

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“…Reductive amination of the aldehyde 2 was achieved by using a combination of a commercially available solution of methylamine in methanol, molecular hydrogen, and Pd-C produced target amine 1. Generally, the two commonly used reductive amination protocols are based on either catalytic hydrogenation or hydride reducing agents; in contrast to hydride reducing agents, the use of molecular hydrogen is economically attractive [28][29][30][31][32][33].…”

Section: Chemical Shift δmentioning

confidence: 99%

1,5-Dichloroethanoanthracene Derivatives As Antidepressant Maprotiline Analogs: Synthesis, DFT Computational Calculations, and Molecular Docking

Sultan¹,

Pillai

Alzahrani

et al. 2022

Journal of Chemistry

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The chlorinated tetracyclic 1,5-dichloro-9,10-dihydro-9,10-ethanoanthracen-12-yl)-N-methylmethanamine 1, a maprotiline analog, has been synthesized via reduction and the Diels–Alder reaction followed by reductive amination of aldehyde 2.1D-NMR (DEPT) and 2D-NMR (HSQC, DQF-COSY) techniques were recruited for structural elucidation in addition to HRMS. Density functional theory calculations were performed to identify the possible isomers of the intermediate compound aldehyde 2; these calculations were in good agreement with experimental results where aldehyde 2 could exist in three isomers with comparable energies. In addition, the side chain of this aldehyde 2 was extended via the Wittig reaction to obtain the unsaturated ester 5 that was subjected to selective olefinic catalytic hydrogenation to obtain the corresponding saturated ester 6. Molecular docking simulation showed that all the compounds (1, 2, 5, and 6) have high antidepressant activities and form stable complexes with LeuT by inhibiting the neurotransmitter reuptake at the synapse and hence are good candidates as antidepressant drugs.

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Reductive amination using a combination of CaH₂ and noble metal

Cited by 13 publications

References 118 publications

Titanium-Mediated Reduction of Carboxamides to Amines with Borane–Ammonia

Titanium-Mediated Reduction of Carboxamides to Amines with Borane–Ammonia

1,5-Dichloroethanoanthracene Derivatives as Antidepressant Maprotiline Analogues: Synthesis and DFT Computational Calculations

1,5-Dichloroethanoanthracene Derivatives As Antidepressant Maprotiline Analogs: Synthesis, DFT Computational Calculations, and Molecular Docking

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Reductive amination using a combination of CaH2 and noble metal

Cited by 13 publications

References 118 publications

Titanium-Mediated Reduction of Carboxamides to Amines with Borane–Ammonia

Titanium-Mediated Reduction of Carboxamides to Amines with Borane–Ammonia

1,5-Dichloroethanoanthracene Derivatives as Antidepressant Maprotiline Analogues: Synthesis and DFT Computational Calculations

1,5-Dichloroethanoanthracene Derivatives As Antidepressant Maprotiline Analogs: Synthesis, DFT Computational Calculations, and Molecular Docking

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Reductive amination using a combination of CaH₂ and noble metal