Ethanol → HCID 86718592, compound

Participants

Reaction Steps

To a solution of 3,6-di-tert-butyl-8-(6-(trifluoromethyl)pyridin-3-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazine (Example 75) (250 mg, 0.63 mmol) in THF (10 mL) under argon was added dropwise a 2.0 M solution of cyclohexylmagnesium chloride in diethyl ether (0.41 mL, 0.82 mmol). The reaction mixture was stirred at room temperature for 16 hours, and then partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried (Na2SO4), filtered, and the crude product purified using flash chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes. The product was dissolved in a 1.25 M solution of hydrochloric acid in ethanol (5 mL, 6.3 mmol), the mixture stirred for 30 minutes then concentrated under reduced pressure and the product triturated with hexane to give 4-(tert-butyl)-2-((tert-butyl(cyclohexylmethyl)amino)methyl)-6-(6-(trifluoromethyl)pyridin-3-yl)phenol hydrochloride (162 mg, 50% yield) as a white powder.

Provenance & Evidence