181293-49-2

Upstream product

• 181293-31-2 (S)-2'-(1-Ethyl-1-methoxy-propyl)-[1,1']bipyrrolidinyl-2-one 
• 181293-15-2 (S)-(-)-4-chloro-N-[2-(1-ethyl-1-methoxypropyl)pyrrolidin-1-yl]butanamide 
• 118535-62-9 (S)-(-)-1-amino-2-(1'-methoxy-1'-ethylpropyl)pyrrolidine 

Downstream Products

• 181293-66-3 (2S)-2-methylphenyl-4-aminobutanoic acid 

Relevant academic research and scientific papers

Enantioselective synthesis of 2-substituted 5-, 6- and 7-membered lactams via α-alkylation of their chiral N-dialkylamino derivatives

2-Alkyl-substituted lactams 4 were synthesized in good overall yields and high enantiomeric purities (ee = 71-99%) by α-alkylation of chiral N-(dialkylamino)lactams 2 and subsequent reductive N-N bond cleavage of the resulting lactams 3 with lithium in liquid ammonia. The lactams 2, in turn, were prepared in good yields by cyclization of ω-chloroalkanohydrazides 1 with sodium hydride. Acidic hydrolysis of lactams 4 leads to γ-aminobutanoic acid (GABA) derivatives 5 (ee ≤ 99%). The absolute configuration was determined by polarimetry and an X-ray structure analysis of (S,S)-3e'.