64838-60-4

Upstream product

• 623-43-8 crotonic acid methyl ester 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 623-43-8 methyl crotonate 
• 618-36-0 rac-methylbenzylamine 

Downstream Products

• 159877-47-1 methyl 3-(R)-[N-(tert-butoxycarbonyl)amino]-propanoate 
• 6078-06-4 (R)-methyl 3-aminobutanoate hydrochloride 
• 3775-73-3 (R)-3-aminobutanoic acid 
• 6078-06-4 (S)-methyl 3-aminobutanoate 

Relevant academic research and scientific papers

Michael additions of amines to methyl acrylates promoted by microwave irradiation

A simple and efficient protocol has been developed for the Michael addition of amines to α,β-unsaturated esters under microwave irradiation. Under these conditions there was a significant decrease in the reaction time, increases in the yields and increased purity of the products.

Enantioselective Synthesis of β-Amino Acids. 5. Stereoselective Reaction of Chiral Pyrimidinone Enolates with Aldehydes

Hydro-pyrimidinones ((2S,6R)-3) and ((2S)-6) were prepared from methyl crotonate via 3-aminobutanoate, and their corresponding lithium enolate and dienolate derivatives were added to various aldehydes.The high regio- and stereoselectivities observed in these aldol reactions pave the road for the preparation of enantiomerically pure β-hydroxy-β'-amino acids.The structures of the products were confirmed by X-ray crystal structure analysis (eight examples).

194. Diastereoselecktive Alkylation of 3-Aminobutanoic Acid in the 2-Position

The enantiomerically pure 3-aminobutanoic acids (R)- and (S)-6 are readily available by preparative HPLC separation of the two diastereoisomers 5 obtained from addition of (S)-phenethylamine to methyl crotonate and subsequent hydrogenolysis (Scheme 2). (S)-methyl 3-(benzoylamino)butanoate ((S)-3) is also available by enzymatic kinetic resolution with pig-liver esterase.The N-benzoyl- and N-benzyloxycarbonyl derivatives rac-3, 8,and 9 of 3-aminobutanoates are doubly deprotonated with LDA and alkylated or aminated in high selectivity (17 examples, relative topicity like; see Tables 1 and 2).The configuration of three of the products is assigned (Schemes 4-6), and in four cases, the free α-substituted β-amino acid is prepared by acidic hydrolysis (see Table 3).It is shown that the doubly lithiated β-amino-acid derivative is solubilized, and its reactivity may be strongly influenced by the presence of 3 equiv. of LiCl.

α-ALKYLATION OF β-AMINOBUTANOATES WITH lk-1,2-INDUCTION

Dilithiated methyl- or ethyl-N-benzoyl-3-aminobutanoates are alkylated or added to benzaldehyde to give products of l- and u,u-configuration respectively.Several methods are presented by which enantiomerically pure 3-aminobutanoic derivatives can be prepared.