1239450-42-0Relevant articles and documents
Efficient preparation of 2,4-methanoproline
Varnes, Jeffrey G.,Lehr, G. Scott,Moore, Gary L.,Hulsizer, James M.,Albert, Jeffrey S.
, p. 3756 - 3758 (2010)
Using a modification of the route described by Clardy and Hughes et al., 2,4-methanoproline hydrochloride (1) was prepared in four steps and 70% overall yield from DL-serine methyl ester.
Synthesizing method using serine to prepare Ramipril key intermediate
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Paragraph 0054; 0055, (2016/10/10)
The invention relates to a synthesizing method using serine to prepare a Ramipril key intermediate. The Ramipril key intermediate is 2-azabicyclo[3.3.0] octane-3-carboxylic acid hydrochloride or benzyl ester hydrochloride. The synthesizing method includes: using the serine as the initial raw material, and sequentially performing esterification, acyl chloride acylation, deacidification, Michael addition, hydrolysis and hydrogenation reduction to obtain the Ramipril key intermediate. The synthesizing method has the advantages that the key intermediate is synthesized by a five-step method, and the synthesizing method is cheap in raw material, environmentally friendly, simple in preparation process, simple to operate, mild in reaction condition, short in reaction cycle, convenient in post-treatment, low in equipment requirement, capable of avoiding heavy metal pollution and the use of expensive catalysts, few in three wastes, high in product yield and purity and suitable for industrial production.
Conversion of isomeric 2:3 adducts (aminoacid-formaldehyde) to N-acyl-pseudoprolines derivatives
Sélambarom, Jimmy,Smadja, Jacqueline,Pavia, André A.
, p. 615 - 617 (2007/10/03)
Reaction of acyl chlorides or acid anhydrides with isomeric 2:3 adducts derived from condensation of l-serine (1a), l-threonine (1b) and l-cysteine (1c) methyl esters with formaldehyde afforded N-acyl-pseudoprolines 7-19 in various yields. These 2:3 adducts can be considered as synthetic equivalents of oxaproline and thiaproline moieties. The present work revealed the versatile behaviour of the two 2:3 adducts as a consequence of the ring-chain tautomerism occurring in the five- and/or seven-membered rings.
New synthesis of 7-azabicyclo[2.2.1]heptane-1-carboxylic acid
Avenoza, Alberto,Cativiela, Carlos,Busto, Jesús H,Fernández-Recio, Miguel A,Peregrina, Jesús M,Rodríguez, Fernando
, p. 545 - 548 (2007/10/03)
This report describes a new synthetic route to 7-azabicyclo[2.2.1]heptane-1-carboxylic acid (Ahc), a constrained proline analogue, in which the key step is the Diels-Alder reaction using methyl 2-benzamidoacrylate as dienophile.