SCH 486757 synthesis

Yield:-

Reaction Conditions:

with n-butyllithium in tetrahydrofuran;hexane

Steps:

1.2 Step 2
Step 2 Add n-BuLi (2.5 M in hexane, 16.5 ml, 41.2 mmol) dropwise to the solution of the product of Step 1 (15 g, 40.6 mmol) in THF (80 ml) at -78° C. and maintain the reaction at this temperature for 45 min. To this solution, add a solution of the product of Preparation 3 (6 g, 16.7 mmol) in THF (30 ml) dropwise and stir the reaction mixture for additional 3 h at -78° C. Warm the reaction mixture to RT over a period of 1.5 h. Pour the reaction mixture on saturated aqueous NH₄Cl and extract with EtOAc. Combine the organic layers, dry and concentrate. Purify the residue by column chromatography to produce the title compound as light white solid. ¹H NMR (CDCl₃) δ8.75 (d, 2H), 7.96 (d, 2H), 7.30 (m, 4H), 7.20 (t, 1H), 7.15 (m, 2H), 5.59 (s, 1H), 4.86 (s, 1H, OH), 3.20 (m, br, 2H), 2.60 (dd, 2H), 2.40 (dd, 2H), 2.24 (m, 2H), 1.68 (d, 2H).

References:

Schering Corporation US2003/119847, 2003, A1