144688-70-0

Basic information

• Product Name: (R)-1-Boc-2-cyanopyrrolidine
• Synonyms: (S)-1-N-BOC-2-CYANO-PYRROLIDINE;(S)-1-N-BOC-2-PYRROLIDINONITRILE;(S)-(-)-BOC-2-PYRROLIDINONITRILE;(S)-(-)-BOC-2-CYANOPYRROLIDINE;(S)-N-BOC-2-PYRROLIDINONITRILE;(R)-1-N-BOC-2-CYANO-PYRROLIDINE;(R)-1-N-BOC-2-PYRROLIDINONITRILE;(R)-(+)-1-BOC-2-PYRROLIDINONITRILE
• CAS NO: 144688-70-0
• Molecular Formula: C₁₀H₁₆N₂O₂
• Molecular Weight: 196.25
• Product Categories: Pyrrolidines;Pyrrole&Pyrrolidine&Pyrroline;Chiral Building Blocks;Heterocyclic Building Blocks
• Mol File: 144688-70-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 33-36 °C(lit.)
• Boiling Point: 307.9 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.08 g/cm³
• Vapor Pressure: 0.000703mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: 2-8°C
• PKA: -4.97±0.40(Predicted)
• CAS DataBase Reference: (R)-1-Boc-2-cyanopyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Boc-2-cyanopyrrolidine(144688-70-0)
• EPA Substance Registry System: (R)-1-Boc-2-cyanopyrrolidine(144688-70-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 144688-70-0(Hazardous Substances Data)

Usage

General Description

(R)-1-Boc-2-cyanopyrrolidine is a chemical compound that belongs to the class of pyrrolidine derivatives. It is characterized by the presence of a Boc (tert-butoxycarbonyl) group and a cyanide group attached to the pyrrolidine ring. (R)-1-Boc-2-cyanopyrrolidine is commonly used as a building block in organic synthesis and medicinal chemistry. The Boc group serves as a protecting group for the amine functionality, enabling selective reactions at other parts of the molecule. The cyanide group can participate in various chemical reactions, adding versatility to the molecule's synthetic applications. Additionally, (R)-1-Boc-2-cyanopyrrolidine has shown potential pharmacological activity and is being investigated for its potential use in drug development. Overall, it is a versatile and valuable compound with applications in both chemical synthesis and medicinal chemistry.

InChI:InChI=1/C10H16N2O2/c1-10(2,3)14-9(13)12-6-4-5-8(12)7-11/h8H,4-6H2,1-3H3/t8-/m1/s1

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 144688-69-7 tert-butyl 2-methoxypyrrolidine-1-carboxylate 
• 54503-10-5 tert-butyl 2-carbamoylpyrrolidine-1-carboxylate 
• 15761-39-4 N-tert-butoxycarbonyl-proline 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 506-68-3 bromocyane 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 

Downstream Products

• 144688-72-2 α-benzyl-N-tert-butoxycarbonyl-α-cyanopyrrolidine 
• 500024-95-3 tert-butyl (Z)-2-(N'-hydroxycarbamimidoyl)pyrrolidine-1-carboxylate 
• 960294-17-1 tert-butyl 2-(3-chloropropyl)-2-cyanopiperidine-1-carboxylate 
• 960294-12-6 tert-butyl 2-(2-chloroethyl)-2-cyanopyrrolidine-1-carboxylate 
• 960294-13-7 tert-butyl 2-(3-chloropropyl)-2-cyanopyrrolidine-1-carboxylate 
• 960294-14-8 tert-butyl 1,7-diazaspiro[4.5]decane-1-carboxylate 
• 885268-47-3 1,7-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester 
• 519031-85-7 methyl 5-(benzoyloxy)-6-hydroxy-2-(pyrrolidin-2-yl)pyrimidine-4-carboxylate 
• 519030-48-9 N-(4-fluorobenzyl)-5,6-dihydroxy-2-(pyrrolidin-2-yl)pyrimidine-4-carboxamide 
• 518047-23-9 methyl 5-(benzoyloxy)-2-[1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-6-hydroxypyrimidine-4-carboxylate 
• 144688-81-3 α-benzyl-N-tert-butoxycarbonylpyrrolidine 
• 1312454-79-7 tert-butyl 2-(aminomethyl)-2-methylpyrrolidine-1-carboxylate 

Relevant articles and documents

Visible-Light-Mediated Alkenylation, Allylation, and Cyanation of Potassium Alkyltrifluoroborates with Organic Photoredox Catalysts

Iridium- and ruthenium-free approaches to protected allylic amines and alkyl nitriles under photoredox conditions are reported. An inexpensive organic dye, eosin Y, catalyzes coupling of Boc-protected potassium α-aminomethyltrifluoroborates with a variety of substituted alkenyl sulfones through an α-aminomethyl radical addition-elimination pathway. Allylic and homoallylic amines were formed in moderate yields with high E/Z selectivity. The mechanistic approach was extended using tosyl cyanide as a radical trap, enabling the conversion of alkyltrifluoroborates to nitriles via a Fukuzumi acridinium-catalyzed process.

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.

C(sp3)?H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis

Inspired by the reaction mechanism of photo-induced DNA cleavage in nature, a C(sp3)?H cyanation reaction promoted by visible-light photoredox/phosphate hybrid catalysis was developed. Phosphate radicals, generated by one-electron photooxidation of phosphate salt, functioned as a hydrogen-atom-transfer catalyst to produce nucleophilic carbon radicals from C(sp3)?H bonds with a high bond-dissociation energy. The resulting carbon radicals were trapped by a cyano radical source (TsCN) to produce the C?H cyanation products. Due to the high functional-group tolerance and versatility of the cyano group, the reaction will be useful for realizing streamlined building block syntheses and late-stage functionalization of drug-like molecules.