112979-60-9

Upstream product

• 83509-86-8 N-benzoyl-3-aminobutyric acid 
• 98-88-4 benzoyl chloride 
• 112979-39-2 methyl N-benzoyl-DL-β-homoalaninate 
• 121006-10-8 (u,u)-3-(Benzoylamino)-2-(1'-hydroxybenzyl)buttersaeure 

Downstream Products

• 124-38-9 carbon dioxide 
• 61247-78-7 (E)-N-(4-phenylbut-3-en-2-yl)benzamide 

Relevant academic research and scientific papers

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.