154279-16-0

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
(±)-N-Boc-2-amino-2-benzylacetonitrile serves as a valuable building block in organic synthesis, particularly within the pharmaceutical and medicinal chemistry fields. Its Boc protecting group can be removed under acidic conditions, enabling further functionalization of the amino group, which is crucial for the development of complex molecular structures.
Used in Organic Synthesis:
In the realm of organic synthesis, (±)-N-Boc-2-amino-2-benzylacetonitrile is utilized as a versatile intermediate. Its benzylacetonitrile moiety confers reactivity towards a broad spectrum of organic reactions, facilitating the production of a diverse array of compounds. This adaptability makes it an essential component in the synthesis of various organic molecules.

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 151-50-8 potassium cyanide 
• 774225-32-0 tert-butyl 2-phenyl-1-(phenylsulfonyl)ethylcarbamate 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 150-30-1 Phenylalanine 

Relevant academic research and scientific papers

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

A convenient synthesis of N-boc-protected α-aminonitriles from α-amidosulfones

Synthesis of N-Boc-protected α-aminonitriles starting from N-Boc-protected α-aminosulfones is described. Treatment of the sulfone with two equivalents of potassium cyanide in 2-propanol or dichloromethane- H2O under phase transfer condition affords crystalline N-Boc-protected α-aminonitriles in good yield. Hydrolysis of the aminonitriles provides a convenient access to racemic α-amino acids.

α-Isocyanatoacrylonitriles from alkylidene- or arylidenecyanoacetic acids; synthesis and reactions

The Curtius reaction converts alkylidene- or arylidenecyanoacetic acids to α-isocyanatoacrylonitriles in a stereospecific way. These versatile intermediates allow an easy access to arylacetic acids and various amino acid derivatives, as well as β-lactams or 2-azabutadienes.