Triacetoxyperiodinane → HCID 86761707, compound

Participants

Reaction Steps

The intermediate from Step D was subjected to the Suzuki conditions described in EXAMPLE 1 Step A to give methyl 4-{3-hydroxy-1-methyl-2-[4′-(trifluoromethoxy)biphenyl-3-yl]propyl}benzoate as a mixture of diastereomers. LCMS1 3.92 min. (M−H2O)=427. LCMS1 4.08 min. (M−H2O)=427. A DCM (2 mL) solution containing 4-{3-hydroxy-1-methyl-2-[4′-(trifluoromethoxy)biphenyl-3-yl]propyl}benzoate (50 mg, 0.1 μmol) was treated with [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one] (64 mg, 0.15 mmol). After stirring for 1 hour the solution was concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compounds as a mixture of diastereomers. 1H NMR (400 MHz, CDCl3): selected data δ 9.84 (d, J=2.3 Hz); 9.64 (d, J=2.3 Hz); 1.44 (d, J=6.7 Hz); 1.14 (d, J=7.0 Hz). LCMS1 4.11 min. (M+H)=443. LCMS1 4.24 min. (M+H)=443.

Provenance & Evidence