Acetic Acid → HCID 58399157, compound

Participants

Reaction Steps

To a solution of 0.8 g of the product of Step 10 in 100 mL of MeOH and 20 mL of THF was added 0.3 g of NaBH4. After stirring for 1 h at room temperature, 2 mL of AcOH was added and the reaction mixture was concentrated and the residue was portioned between 50 mL of brine and 150 mL of EtOAc. The organic layer was separated and dried over Na2SO4. After filtration, the filtrate was concentrated and the residue was dissolved in 5 mL of CH2Cl2, and treated with 5 mL of Et3SiH and 3 mL of TFA. After stirring for 30 min at room temperature, the reaction mixture was concentrated and the residue was purified by Combiflash eluted with a gradient up to 70% EtOAc/hexane to give 0.3 g of the title compound. 1H NMR (500 MHz, acetone-d6) δ 8.10 (m, 2H), 7.45-7.52 (m, 3H), 7.27 (d, 1H), 7.10 (m, 1H), 7.01 (m, 1H), 4.53 (m, 1H), 4.18 (m, 1H), 3.88 (t, 1H), 3.60 (s, 3H), 3.13 (m, 1H), 2.97 (s, 3H), 2.86 (m, 1H), 1.90-2.00 (m, 1H), 1.70 (m, 1H).

Provenance & Evidence