{(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester → (R)-7-Fluoro-1-[(S)-3-methoxycarbonylmethyl-2,3-dihydrobenzofuran-6-yloxy]-2,3-dihydro-1H-inden-4-ylboronic acid

Participants

Reaction Steps

{(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (3.00 g) is dissolved in acetone (20 mL) and water (10 mL). NaIO4 (5.90 g) and NH4O2CCH3 (2.85 g) are added. The mixture is stirred at room temperature for 36 h. Water is added and the resulting mixture is extracted with ethyl acetate. The combined extract is dried (Na2SO4) and concentrated to give the title compound LC (method 12): tR=1.02 min; Mass spectrum (ESI+): m/z=387 [M+H]+.

Provenance & Evidence