Tetrabutylammonium Fluoride → HCID 57888692, compound

Participants

Reaction Steps

A solution of 2-(trimethylsilyl)ethyl (2R)-1-(8-(4-chlorophenyl)-8-hydroxy-5-azaspiro[2.5]octan-5-yl)-3-methyl-1-oxobutan-2-ylcarbamate (754 mg, 1.567 mmol) in THF (10 mL) was treated with TBAF (1.0 M in THF) (6.27 mL, 6.27 mmol), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated in-vacuo, and the residue was partitioned between EtOAc and saturated sodium bicarbonate. The layers were separated, and the organic phase was washed 2× with saturate sodium bicarbonate, once with water, and once with brine. The combined aqueous phases were extracted once with ethyl acetate, and the combined organic phases were washed with water and brine, then dried over sodium sulfate and concentrated in-vacuo. The residue was taken up in acetonitrile (100 mL), and washed 3× with 20 mL of hexanes. The acetonitrile phase was concentrated in-vacuo to yield the title compound (420 mg, 1.247 mmol, 80% yield) as a colorless glass. MS (ESI+)=337.4, (M+H)+.

Provenance & Evidence