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;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem