7619-17-2Relevant articles and documents
Metaraminol bitartrate enantiomer synthesis method
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Paragraph 0008; 0021; 0023, (2019/11/20)
The invention discloses a metaraminol bitartrate enantiomer synthesis method, which comprises: 1, carrying out an addition reaction on nitroethane and m-hydroxybenzaldehyde to obtain a 3-(1-hydroxy-2-nitro-propyl)-phenol racemate; 2, purifying to obtain 3
Enzymatic and Chemoenzymatic Three-Step Cascades for the Synthesis of Stereochemically Complementary Trisubstituted Tetrahydroisoquinolines
Erdmann, Vanessa,Lichman, Benjamin R.,Zhao, Jianxiong,Simon, Robert C.,Kroutil, Wolfgang,Ward, John M.,Hailes, Helen C.,Rother, D?rte
supporting information, p. 12503 - 12507 (2017/09/13)
Chemoenzymatic and enzymatic cascade reactions enable the synthesis of complex stereocomplementary 1,3,4-trisubstituted tetrahydroisoquinolines (THIQs) with three chiral centers in a step-efficient and selective manner without intermediate purification. The cascade employs inexpensive substrates (3-hydroxybenzaldehyde and pyruvate), and involves a carboligation step, a subsequent transamination, and finally a Pictet–Spengler reaction with a carbonyl cosubstrate. Appropriate selection of the carboligase and transaminase enzymes enabled the biocatalytic formation of (1R,2S)-metaraminol. Subsequent cyclization catalyzed either enzymatically by a norcoclaurine synthase or chemically by phosphate resulted in opposite stereoselectivities in the products at the C1 position, thus providing access to both orientations of the THIQ C1 substituent. This highlights the importance of selecting from both chemo- and biocatalysts for optimal results.
Method for synthesizing metaraminol bitartrate
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Paragraph 0019; 0022, (2017/11/18)
The invention provides a process for synthesizing metaraminol bitartrate. The process comprises the following steps: taking carbobenzoxy-L-alanine as a raw material, carrying out a cyclization reaction, and carrying out a reaction with a Grignard reagent so as to prepare an intermediate (4S)-N-carbobenzoxy-5-(3-(benzyloxy)phenyl)-5-hydroxy-4-methyloxazolane; carrying out a hydrolytic ring-opening reaction on the intermediate, and producing (2S)-2-(carbobenzoxy)amino-1-(3-benzyloxyphenyl)-1-acetone; carrying out a reduction reaction on the (2S)-2-(carbobenzoxy)amino-1-(3-benzyloxyphenyl)-1-acetone so as to obtain (1R,2S)-2-(carbobenzoxy)amino-1-(3-benzyloxyphenyl)-1-propanol; performing deprotection on the (1R,2S)-2-(carbobenzoxy)amino-1-(3-benzyloxyphenyl)-1-propanol so as to obtain metaraminol; finally, performing salt formation on metaraminol and L-tartaric acid, thereby obtaining the metaraminol bitartrate. According to the method disclosed by the invention, usage of an expensive catalyst and chiral resolution can be avoided, and the cost is greatly reduced; by utilizing chemical synthesis, industrial production of optical pure metaraminol bitartrate becomes possible.