963-75-7Relevant articles and documents
Vecuronium bromide and its advanced intermediates: A crystallographic and spectroscopic study
Ciceri, Samuele,Colombo, Diego,Ferraboschi, Patrizia,Grisenti, Paride,Iannone, Marco,Mori, Matteo,Meneghetti, Fiorella
, (2021/10/25)
Vecuronium bromide (Piperidinium, 1-[(2β,3α,5α,16β,17β)-3,17-bis(acetyloxy)-2-(1-piperidinyl)androstan-16-yl]-1-methyl-, bromide; Norcuron) has been extensively used in anesthesiology practice as neuromuscular blocking agent since its launch on the market in 1982. However, a detailed crystallographic and NMR analysis of its advanced synthetic intermediates is still lacking. Hence, with the aim of filling this literature gap, vecuronium bromide was prepared starting from the commercially available 3β-hydroxy-5α-androstan-17-one (epiandrosterone), implementing some modifications to a traditional synthetic procedure. A careful NMR study allowed the complete assignment of the 1H, 13C, and 15N NMR signals of vecuronium bromide and its synthetic intermediates. The structural and stereochemical characterization of 2β,16β-bispiperidino-5α-androstane-3α,17β-diol, the first advanced synthetic intermediate carrying all the stereocenters in the final configuration, was described by means of single-crystal X-ray diffraction and Hirshfeld surface analysis, allowing a detailed conformational investigation.
Preparation method of 5alpha-androstane-2-ene-17 ketone
-
Paragraph 0025-0030, (2021/11/14)
The invention discloses a preparation method of a skeletal muscle relaxant drug intermediate 5 alpha-androstane-2-ene-17 ketone, and belongs to the technical field of synthesis. According to the method disclosed by the invention, epiandrosterone is taken as a raw material and reacts with p-dodecyl benzene sulfonyl chloride under the action of a catalyst to generate sulfonate, and the 5alpha-androstane-2-ene-17 ketone is generated by elmination. The synthesis method provided by the invention can effectively reduce a double-bond position isomer 5 [alpha]-androstane-3-ene-17 ketone of the target product 5 [alpha]-androstane-2-ene-17 ketone, greatly improves the product quality, and reduces the production cost at the same time.
Preparation method of 5 alpha-androstane-2-ethylene-17-ketone
-
Paragraph 0021-0024; 0025-0026; 0027-0028; 0029-0044, (2019/05/08)
The invention discloses a preparation method of 5 alpha-androstane-2-ethylene-17-ketone. The preparation method comprises the steps of taking epiandrosterone (formula I as shown in the specification)as a raw material to give a dehydration reaction by joint catalysis of protonic acid and trifluoromethanesulfonate, and performing post-treatment, recrystallization and separation on a reaction product to form 5 alpha-androstane-2-ethylene-17-ketone (formula II as shown in the specification). The preparation method avoids the use of much organic base compound in the traditional method, has the advantages of high reaction yield, short procedure, good selectivity, low cost, less waste gas, waste water and industrial residue and the like and is a synthesis method suitable for industrial production.