Sodium borohydride → HCID 22324721, compound

Participants

Reaction Steps

To a stirred solution of 2-oxo-2-pyridin-2-yl-O-(tetrahydro-2H-pyran-2-yl)ethanol (1.15 g, 0.00520 mol) in methanol at 0° C. is added sodium borohydride (0.195 g, 0.00515 mol) in portions. The reaction is stirred for 2.5 hours and rotary evaporated to dryness. The residue is dissolved in ethyl ether, washed with brine (3×), dried (Na2SO4), and rotary evaporated. The residue is purified by chromatography on silica gel (50 g, 230-400 mesh), eluting with hexanes-ethyl acetate (1:1) to give 0.84 g of (±)-1-pyridin-2-yl-2-(tetrahydro-2H-pyran-2-yloxy)-ethanol as a pale yellow oil. MS-APCI m/z 224 [M−H]+. 4. (±)-6-(2-Tetrahydro-2H-1-pyran-2-yloxy-1-(2-pyridyl)ethoxy)-5-(2-phenylethyl)-2,3,4-trihydronaphthalen-1-one

Provenance & Evidence