Triacetoxyperiodinane → 3-(2-Acetyl-8-fluoro-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-3-yl)propanal

Participants

Reaction Steps

1-[8-Fluoro-3-(3-hydroxypropyl)-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-2-yl]ethanone (5-8; a racemic mixture, 1.23 g, 3.34 mmol) was dissolved in anhydrous CH2Cl2 (20 mL) and was treated with Dess-Martin periodinane (2.26 g, 5.3 mmol) and the resulting cloudy yellow solution was stirred 1.5 h. Upon completion, the cloudy solution was treated with 10 mL sat. sodium thiosulfate/NaHCO3 solution (1:1) and stirred 30 min. The mixture was extracted with EtOAc (3×20 mL), and the combined organics were dried (MgSO4), filtered and concentrated. The crude residue 3-(2-acetyl-8-fluoro-3-phenyl-3a,4-dihydro-3H-pyrazolo[5,1-c][1,4]benzoxazin-3-yl)propanal (5-9; a racemic mixture) was carried directly into the next transformation: MS (M+H+, C21H19FN2O3) 367.3 found 367.4 required.

Provenance & Evidence