1283095-48-6 tert-Butyl 4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran]-1-carboxylate 52951550, apiperidines compound, is more and more widely used in various fields.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1283095-48-6,tert-Butyl 4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran]-1-carboxylate,as a common compound, the synthetic route is as follows.
2,2,6,6-Tetramethylpiperidine (18.7 mL, 1 10.5 mmol) is added overtetrahydrofuran (200 mL), and solution is cooled under nitrogen at -78C. 2.5 M solution of butyl lithium in hexane (37.2 mL, 93 mmol) is added and mixture is stirred for 30 min at -78C. Over the fresh lithium 2,2,6,6-tetramethylpiperidine solution is added a solution of tert-butyl spiro[4,5-dihydrothieno[2,3-c]pyran-7,4′-piperidine]-l’- carboxylate (20 g, 58.2 mmol) in tetrahydrofuran (90 mL) keeping temperature below -70C. After 20 min a solution of N-fluorobenzenesulfonimide (30.26 g, 93.07 mmol) in tetrahydrofuran (200 mL) previously cooled under nitrogen at -20C is added via cannula. After 1 hr. stirring, water (20 mL) and aqueous solution of ammonium chloride (50 mL) are added. Then, organic layer is separated and the aqueous is washed twice with methyl t-butyl ether (2 x 25 mL). Organics are combined and solvent is evaporated under reduced pressure. Crude material is purified by normal phase HPLC using hexane/ methyl t-butyl ether as solvents to give tert-butyl 2- fluorospiro[4,5-dihydrothieno[2,3-c]pyran-7,4′-piperidine]-r-carboxylate in 50% yield. MS (m/z): 328 (M+l)., 1283095-48-6
1283095-48-6 tert-Butyl 4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran]-1-carboxylate 52951550, apiperidines compound, is more and more widely used in various fields.
Reference£º
Patent; ELI LILLY AND COMPANY; BENITO COLLADO, Ana Belen; DIAZ BUEZO, Nuria; JIMENEZ-AGUADO, Alma Maria; LAFUENTE BLANCO, Celia; MARTINEZ-GRAU, Maria Angeles; PEDREGAL-TERCERO, Concepcion; TOLEDO ESCRIBANO, Miguel Angel; WO2011/60217; (2011); A1;,
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