253168-94-4Relevant articles and documents
Synthetic method of apremilast intermediate
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Paragraph 0018; 0035-0036, (2021/04/26)
The invention discloses a synthetic method of an apremilast intermediate. The method comprises the following steps of by taking 2-methoxyphenyl acetate and 2-(methylsulfonyl) acetyl chloride as starting materials, carrying out acylation reaction and hydrolysis under the catalysis of aluminum trichloride to obtain 1-(3-hydroxy-4-methoxyphenyl)-2-(methylsulfonyl) ethyl ketone, carrying out alkylation reaction with bromoethane, and then forming imine with ammonium acetate, and reducing to form the 1-(3-ethoxy-4-methoxy phenyl)-2-(methylsulfonyl) ethylamine. The method is simple to operate, avoids the use of n-butyllithium, palladium on carbon and mesylate, avoids the problems of high risk, high cost and the like, and is suitable for industrial production.
RACEMIC BETA-AMINOSULFONE COMPOUNDS
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, (2020/03/28)
It is described an industrially viable and advantageous process for the preparation of racemic beta-aminosulfone (1), an useful intermediate for the preparation of N-(2-((1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl)acetamide, also known as Apremilast, the latter being suitable for use in methods of treating, preventing and/or managing psoriasis or psoriatic arthritis.
Synthesis of Substituted β-Functionalised Styrenes by Microwave-Assisted Olefin Cross-Metathesis and Scalable Synthesis of Apremilast
Jana, Anupam,Zieliński, Grzegorz Krzysztof,Czarnocka-?niada?a, Sylwia,Grudzień, Krzysztof,Podwysocka, Dominika,Szulc, Marcin,Kajetanowicz, Anna,Grela, Karol
, p. 5808 - 5813 (2019/11/03)
Preparation of diversely substituted β-functionalised styrenes by microwave-assisted olefin cross-metathesis (CM) is described. This method can be also employed in the synthesis of β-deuterated α,β-unsaturated sulfones from inexpensive allylbenzenes, though unprecedented one-pot isomerisation/deuteration/cross-metathesis sequence. One of such obtained CM products has been utilised in a new scalable synthesis of Apremilast (6), a potent and orally active phosphodiesterase 4 and tumour necrosis factor-α inhibitor. The same strategy was used in synthesis of an optical antipode of 6, ent-Apremilast.