181376-74-9

Basic information

• Product Name: Acetamide, N-(1-cyano-2-phenylethyl)-, (R)-
• CAS NO: 181376-74-9
• Molecular Formula: C11H12N2O
• Molecular Weight: 188.229
• Mol File: 181376-74-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Acetamide, N-(1-cyano-2-phenylethyl)-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, N-(1-cyano-2-phenylethyl)-, (R)-(181376-74-9)
• EPA Substance Registry System: Acetamide, N-(1-cyano-2-phenylethyl)-, (R)-(181376-74-9)

Safety Data

• Hazardous Substances Data: 181376-74-9(Hazardous Substances Data)

Upstream product

• 108-21-4 Isopropyl acetate 
• 55379-75-4 2-amino-3-phenylpropanenitrile 
• 7376-89-8 AcFNH₂ 
• 141-78-6 ethyl acetate 
• 66913-75-5 2-cyano-3-phenylaziridine 
• 176847-60-2 2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-((2S,3S)-2-phenyl-3-trimethylsilanyl-aziridin-1-yl)-3H-quinazolin-4-one 
• 177018-15-4 (2R,3S)-2-cyano-3-phenylaziridine 
• 108-24-7 acetic anhydride 
• 159517-27-8 (R)-2-amino-3-phenylpropanenitrile 
• 64300-27-2 (+/-)-trans-3-phenylaziridine-2-carbonitrile 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Acceptor-Controlled Transfer Dehydration of Amides to Nitriles

Palladium-catalyzed dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired scheme exergonic, thereby driving the dehydration.

Process for the preparation of enantiomerically enriched compounds

1. Process for the preparation of enantiomerically enriched amino aldehydes and amino alcohols, wherein a corresponding enantiomerically enriched amino nitrile is subjected to hydrogenation in the presence of hydrogen, a hydrogenation catalyst, preferably a Pd-catalyst and a mineral acid. For the preparation of an amino aldehyde hydrogen preferably is present at a hydrogen-pressure between 0.1 and 2 MPa, in particular between 0.5 and 1 MPa. The amino aldehyde preferably is isolated in the form of a chemically and configurationally stable derivative. For the preparation of an amino alcohol, preferably at least during part of the hydrogenation hydrogen is present at a hydrogen-pressure between 2 and 10 MPa, in particular between 4 and 6 MPa. In a preferred embodiment the hydrogen-pressure initially is between 0,5 and 2 MPa and subsequently, after most of the nitrile starting material is converted, the hydrogen pressure is increased to a value between 2 and 10 MPa. The enantiomerically enriched nitrile starting material may a.o. be prepared by enzymatic resolution, classical resolution, resolution via preferential crystallization, diastereomeric synthesis, catalytic asymmetric synthesis or dehydratation of amino acid amides.

Preparation of N-H aziridines in high enantiomeric excess by in situ aziridine-azirine-aziridine interconversion

Aziridine 6 is produced highly diastereoselectively by treatment of enantiopure 3-acetoxyaminoquinazolinone 4 (Q*NHOAc) with β-trimethylsilylstyrene: desilylative elimination of Q* and in situ addition of cyanide to the intermediate azirine gives the NH-a