35341-76-5

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 19145-06-3 (S)-N-formyl-1-phenylethylamine 
• 300843-73-6 (1S)-((1-phenylethyl)imino)acetonitrile N-oxide 
• 78798-33-1 (S)-N-hydroxy-α-methyl-benzenemethanamine ethanedioate 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 300843-73-6 (S,Z)-N-(cyanomethylene)-1-phenylethanamine oxide 
• 300843-73-6 (1S)-((1-phenylethyl)imino)acetonitrile N-oxide 
• 53933-47-4 N-((1S)-1-phenylethyl)hydroxylamine 

Relevant academic research and scientific papers

Iron-catalyzed reductive strecker reaction

Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.

Conjugate addition of lithium N-tert-butyldimethylsilyloxy-N-(α-methylbenzyl)amide: asymmetric synthesis of β2,2,3-trisubstituted amino acids

Conjugate addition of the homochiral ammonia equivalent lithium N-tert-butyldimethylsilyloxy-N-(α-methylbenzyl)amide to a range of α,β-unsaturated esters gives the corresponding β-amino esters in moderate to good levels of diastereoselectivity. O-Desilylation and cyclisation furnishes homochiral isoxazolidin-5-ones in >99:1 dr after purification. Sequential alkylation of these templates proceeds to give the corresponding 3,4-anti-disubstituted and 3,4,4-trisubstituted derivatives as single diastereoisomers after purification. The first alkylation occurs with high levels of diastereoselectivity on the face of the enolate anti to the C(3)-substituent, whereas the facial selectivity of the second alkylation is governed by a chiral relay effect, which depends upon the relative steric bulk of both the C(3)- and C(4)-substituents. Subsequent hydrogenolysis promotes cleavage of both the N-α-methylbenzyl group and the N-O bond within the isoxazolidin-5-one ring in one pot to give the corresponding β2,2,3-trisubstituted amino acids directly.

An improved process for the synthesis and isolation of (S)-N-(1- phenylettiyl)hydroxylamine

A three-step, single-solvent telescoped process amenable to the large-scale manufacture of (S)-N-(1-phenylethyl)hydroxylamine p-toluenesulfonic acid salt is reported. This synthetic protocol has been applied to the preparation of other chiral hydroxylamin

Chemical process

A process for preparing a salt of compound of formula (I) wherein R1 and R2 are independently selected from an organic group other than hydrogen, said process comprising reacting a compound of formula (II) with water and an organic a

A novel transformation of primary amines to N-monoalkylhydroxylamines

A novel transformation of primary amines to the corresponding N-monoalkylhydroxylamines is described. The three-step protocol involves selective mono-cyanomethylation of primary amines, regioselective formation of nitrones by m-CPBA oxidation, and hydroxylaminolysis of the nitrones with hydroxylamine hydrochloride. The method is applicable for a wide range of primary amines, including alkyl, benzyl, and chiral.