Sodium hydride → N-((S)-7-fluoro-2,2-dimethyl-6-neopentyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-yl)-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

To a 150 mL RBF was added N—((S)-2-(1-(tert-butyldimethylsilyloxy)cyclobutyl)-1-(2,6-difluoro-5-neopentylpyridin-3-yl)ethyl)-2-methylpropane-2-sulfinamide (0.070 g, 0.14 mmol), THF (3 mL), and TBAF, 1M in THF (0.14 ml, 0.14 mmol). The reaction was stirred at RT. After 20 minutes, the reaction was eluted through a plug of silica gel with THF. The resulting filtrate was concentrated in vacuo and taken up in THF (20 mL) and treated with NaH (0.035 g, 0.88 mmol, 60% in mineral oil). The reaction was stirred at 40° C. for 16 hours. The reaction was allowed to cool to RT and quenched with sat'd NH4Cl, and extracted with EtOAc (25 mL). The combined organic layers were concentrated in vacuo to give N—((S)-7-fluoro-2,2-dimethyl-6-neopentyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-yl)-2-methylpropane-2-sulfinamide. This material was carried forward without further purification. MS m/z: 383 (M+1).

Provenance & Evidence