Tetrabutylammonium Fluoride → (R)-3'-(4-Bromofuran-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

Participants

Reaction Conditions

Reaction Steps

Tetra-n-butylammonium fluoride (1M solution in tetrahydrofuran, 2.2 mL, 2.20 mmol) was added to a solution of (R)-3′-[4-bromo-5-(trimethylsilyl)furan-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one (577 mg, 1.44 mmol) in tetrahydrofuran (5 mL). The solution was heated at 70° C. (bath temperature) for 6 h. The reaction mixture was evaporated to dryness, and the residue was subjected to flash chromatography using a gradient of ammoniated methanol in chloroform as the eluant give the title compound as a pale brown solid (387 mg), m/z 327, 329 (MH+).

Provenance & Evidence