(S)-tert-Butyl (1-cyanopropan-2-yl)carbamate
[CAS# 172695-22-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: (S)-tert-Butyl (1-cyanopropan-2-yl)carbamate
• Synonyms: tert-butyl N-[(2S)-1-cyanopropan-2-yl]carbamate
• Molecular Formula: C₉H₁₆N₂O₂
• Molecular Weight: 184.24
• CAS Registry Number: 172695-22-6
• SMILES: C[C@@H](CC#N)NC(=O)OC(C)(C)C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 309.5±25.0 ºC 760 mmHg (Calc.)^*
• Flash point: 141.0±23.2 ºC (Calc.)^*
• Index of refraction: 1.447 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

The chemical substance (S)-tert-butyl (1-cyanopropan-2-yl)carbamate, commonly referred to as a Boc-protected amino nitrile, is a significant compound in organic chemistry, particularly in the synthesis of pharmaceuticals and amino acid derivatives. Its discovery and applications are well-documented in the chemical literature, rooted in the broader development of carbamate protecting groups and chiral synthesis techniques.

The compound’s origins trace back to advancements in organic synthesis during the mid-20th century, when chemists sought reliable methods to protect amine functionalities during multi-step syntheses. The tert-butoxycarbonyl (Boc) group, introduced in the 1950s by researchers like Louis Carpino, emerged as a versatile protecting group due to its stability under basic conditions and ease of removal under mild acidic conditions. The specific compound, (S)-tert-butyl (1-cyanopropan-2-yl)carbamate, is a derivative incorporating the Boc group attached to a chiral amino nitrile framework. The nitrile group, a key functional group, was recognized in the early 20th century for its utility in synthesizing carboxylic acids, amines, and other nitrogen-containing compounds. The chiral (S)-configuration of this molecule reflects advancements in stereoselective synthesis, particularly the use of chiral auxiliaries and catalysts, which became prominent in the 1970s and 1980s to produce enantiopure compounds essential for biological activity.

The synthesis of (S)-tert-butyl (1-cyanopropan-2-yl)carbamate typically involves the protection of a chiral amino alcohol or amine precursor with a Boc group, followed by the introduction of a cyano group via nucleophilic substitution or dehydration reactions. For example, starting from (S)-alaninol or a related chiral precursor, the amine is reacted with di-tert-butyl dicarbonate to install the Boc group, and subsequent transformations, such as conversion to a nitrile via a halide intermediate, yield the target compound. These methods leverage well-established reactions, ensuring high stereochemical purity, which is critical for applications in drug synthesis.

The primary application of (S)-tert-butyl (1-cyanopropan-2-yl)carbamate lies in its role as a synthetic intermediate in pharmaceutical chemistry. The Boc group protects the amine during reactions involving the nitrile, which can be hydrolyzed to form carboxylic acids or reduced to primary amines. These transformations are crucial for synthesizing amino acids, peptides, and other nitrogen-containing bioactive molecules. The chiral (S)-configuration is particularly valuable in producing enantiopure drugs, as the stereochemistry of a molecule often determines its pharmacological efficacy. For instance, this compound serves as a precursor in the synthesis of protease inhibitors and other therapeutic agents where chirality influences binding to biological targets.

Beyond pharmaceuticals, the compound finds use in academic research for studying stereoselective reactions and developing new synthetic methodologies. Its nitrile group is a versatile handle for exploring carbon-carbon bond-forming reactions, such as additions of organometallic reagents, while the Boc group allows chemists to manipulate other parts of the molecule without affecting the amine. The compound’s stability and reactivity make it a model substrate in investigations of asymmetric catalysis and novel protecting group strategies.

The significance of (S)-tert-butyl (1-cyanopropan-2-yl)carbamate lies in its contribution to the efficient and selective synthesis of complex molecules. Its development reflects decades of progress in organic chemistry, from the establishment of protecting group strategies to the refinement of chiral synthesis. By enabling the production of enantiopure intermediates, it has facilitated the creation of safer and more effective drugs, underscoring its importance in both industrial and academic settings.