Toluene → [4-[(2-Chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)methyl]-1-(3-fluoro-2-pyridyl)pyrazol-3-yl]methanol

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Reaction Steps

To a solution of ethyl 4-[(2-chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine]-1′-yl)methyl]-1-(3-fluoro-2-pyridyl)pyrazole-3-carboxylate (2.6 g, 4.93 mmoles) in Tetrahydrofuran (26.00 mL) under N2 atmosphere and cooled to −10 C, Diisobutylaluminum Hydride 1M in toluene (23.68 mL, 23.68 mmoles) is added slowly dropwise. Then, reaction mixture is stirred at that T 15 min and then, the cold bath is removed and the mixture is warmed to room temperature. Then, H2O (100 mL) is added dropwise at −10° C. The resulting suspension is extracted with EtOAc (2×30 mL). Combined organics are washed with H2O (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated to afford a light brown oil that is dissolved in methyl t-butyl ether (10 mL) and white crystals crystallized. Suspension formed is stirred and hexane (10 mL) is added dropwise while stirring. Solid is filtered to give 2 g of the title compound. MS (m/z): 485 (M+1).

Provenance & Evidence