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Efficient enantioconvergent synthesis of (S)-α-benzyl-α-methyl-β-alanine from (R)- and (S)-2-cyano-2-methyl-3-phenylpropanoic acid

✍ Scribed by Ramón Badorrey; Carlos Cativiela; Marı́a D. Dı́az-de-Villegas; José A. Gálvez; Ana Gil

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
256 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

An efficient synthesis of (S)-a-benzyl-a-methyl-b-alanine in 59% overall yield from benzaldehyde and methyl cyanoacetate has been developed. Enantioconvergent approaches to the synthesis of the target a,a-disubstituted b-amino acid from both enantiomers of previously resolved 2-cyano-2-methyl-3-phenylpropanoic acid constitute the key steps in the proposed methodology. The use of inexpensive and readily available reagents and the simplicity of the experimental procedures make the present protocol synthetically attractive and of great potential for scale up.

📜 SIMILAR VOLUMES

Efficient resolution of rac-2-cyano-2-me
Efficient resolution of rac-2-cyano-2-methyl-3-phenylpropanoic acid. An appropriate starting material for the enantioconvergent synthesis of (S)-α-methylphenylalanine on a large laboratory scale
✍ Ramón Badorrey; Carlos Cativiela; Marı́a D. Dı́az-de-Villegas; José A. Gálvez 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 369 KB

A large laboratory scale synthesis of (S)-a-methylphenylalanine from benzaldehyde and methyl cyanoacetate has been developed. The synthesis is based on the following sequence: (i) preparation of racemic 2-cyano-2-methyl-3-phenylpropanoic acid, (ii) resolution of the enantiomers by crystallisation us