Methanol → HCID 71257347, compound

Participants

Reaction Steps

Methyl 2-[6-(1,4-dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl]-2-methylpropanoate (0.299 g, 0.739 mmol) was dissolved in tetrahydrofuran (6 mL, 80 mmol). Sodium tetrahydroborate was then added (70. mg, 1.8 mmol), followed by methanol (450 μL, 11 mmol) in portions. The reaction mixture was stirred 30 min, at which point LCMS showed 50% conversion. After 2 h, LCMS showed no remaining ester, and showed the product (M+H 377), and several over-reduction by-products. The reaction was quenched with water, the solvent removed by rotary evaporation. Aqueous bicarbonate was added, and then EtOAc was added. The mixture was then stirred 0.5 h. The EtOAc layer was shaken with brine, dried (Na2SO4), and the solvent removed by rotary evaporation. The product was purified by automatic silica gel chromatography on a 40 g silica gel column, using solvent A=hexane; solvent B=2% iPA/EtOAc; flow 40 mL/min; A, 2 min; gradient to 30% B in 35 min; detector set at 254 nm; retention time, 26 min. The solvent was removed by rotary evaporation to yield 230 mg of a colorless viscous oil.

Provenance & Evidence