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関連する概念動画

Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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関連する実験動画

Updated: Jun 21, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

直接非対称的還元性アミナーション

Dietrich Steinhuebel1, Yongkui Sun, Kazuhiko Matsumura

  • 1Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA. dietrich_steinhuebel@merck.com

Journal of the American Chemical Society
|July 30, 2009
PubMed
まとめ

ルテニウム (Ru) のキラル触媒を用いた新しい触媒法により,β-ケトアミドの高効率な非対称的還元性アミネーションが可能になった. このプロセスは,シタグリプチンの合成を含む,優れたエナチオ選択性を持つ無保護ベータアミノアミドを生成します.

科学分野:

  • 有機化学 オーガニック・ケミストリー
  • カタリシス カタリシス カタリシス
  • アシンメトリック・シンセシス

背景:

  • ベータ・ケトアミドは,汎用性の高い合成中間物質である.
  • キラルベータアミノアミドを合成するための効率的な方法の開発は,医薬品化学において極めて重要です.
  • 既存の方法は,基板の適用範囲が限られているか,保護/無保護のステップを必要とする可能性があります.

研究 の 目的:

  • 保護されていないβ-アミノアミドの直接合成のための高度にエナンチオセレクティブで効率的な方法を開発する.
  • 非対称的還元性アミネーションのための特定のキラルルテニウム触媒システムの有用性を調査する.
  • 薬学的に重要な化合物であるシタグリプトンの合成におけるこの方法の適用を実証する.

主な方法:

  • ベータ・ケトアミドの非対称的還元性アミネーションは,キラルルテニウム触媒,特にRu (((OAc) 2 ((((R) -dm-セグフォスを使用します).
  • ワンポット反応手順が採用されました.
  • 反応条件は,収穫量,化学選択性,およびエナチオ選択性のために最適化されました.

主要な成果:

  • 保護されていないβ-アミノアミドの範囲では,高収量と優れたエナチオ選択性 (94.7~99.5% ee) が達成されました.

さらに関連する動画

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

関連する実験動画

Last Updated: Jun 21, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

  • 方法論は,広範囲の基板の適用範囲を示した.
  • シタグリプチンは,このワンポットアプローチを使用して99.5%のEEと91%の測定率で合成されました.
  • ルテニウム触媒システムは,アンモニアイオンに対する高い耐性,高い化学選択性,および高いエナチオ選択性を示した.

    • 結論:

    • 開発された非対称的還元性アミネーションは,保護されていないβ-アミノアミドを生成するための非常に効率的でエナンチオセレクティブな方法です.
    • ワンポット・メソドロジーは,複雑なキラルアミンを合成するための実用的でスケーラブルな経路を提供します.
    • この触媒系は,シタグリプチンなどの活性薬剤成分を合成するための貴重なツールです.