In an article, author is Stumpf, Andreas, once mentioned the application of 2403-88-5, Recommanded Product: 2,2,6,6-Tetramethyl-4-piperidinol, Name is 2,2,6,6-Tetramethyl-4-piperidinol, molecular formula is C9H19NO, molecular weight is 157.25, MDL number is MFCD00005983, category is piperidines. Now introduce a scientific discovery about this category.
Practical Early Development Synthesis of Nav1.7 Inhibitor GDC-0310
The concise early development route to the Nav1.7 inhibitor GDC-0310 is described. The active pharmaceutical ingredient (API) contains one stereocenter, which was obtained with high enantiomeric excess (>99:1) by using an S(N)2 displacement approach to connect two intermediates: a chiral benzyl alcohol and a piperidine. The synthesis of the piperidine building block proceeded via a regioselective SNAr reaction on 1-chloro-2,4-difluorobenzene byN-Boc-4-piperidinemethanol, followed by installation of the methyl ester group by electrophilic aromatic bromination and a palladium-catalyzed alkoxycarbonylation. A subsequent Suzuki-Miyaura cross-coupling reaction was then telescoped directly into cleavage of the Boc group to provide the advanced piperidine intermediate. The key feature of the synthesis is the highly selective S(N)2 displacement of the chiral mesylate of (R)-1-(3,5-dichlorophenyl)ethan-1-ol with the piperidine intermediate, followed by a chiral purity upgrade via the corresponding (1S)-(+)-camphorsulfonic acid salt. After standard hydrolysis of the methyl ester and CDI mediated amidation to couple the resulting acid with methanesulfonamide, enantiomerically pure GDC-0310 was obtained in high overall yield (37%) on a 6.5 kilogram scale.
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Reference:
Piperidine – Wikipedia,
,Piperidine | C5H11N – PubChem