Yield:22062-54-0 92.5%

Reaction Conditions:

with sodium tetrahydroborate in ethanol at 20; for 3 h;

Steps:

General procedure for the preparation of 14a, 17a-17d

General procedure: To a solution of substituted phenylaldehyde 13, 15a-15d (8 mmol) in anhydrous ethyl alcohol (12 ml) was added 96% NaBH₄ (0.32 g, 8 mmol) and then stirred at room temperature for 3.0 h. After the solvent was evaporated, the residue was extracted with ethyl acetate, washed with brine and dried over Na₂SO₄. The organic layer was concentrated under reduced pressure to afford 14a, 17a-17d as pale yellow oils. The 14a, 17a-17d were used directly for the next step without further purification.

References:

Li, Yali;Huang, Taomin;Lou, Bin;Ye, Deyong;Qi, Xiangyu;Li, Xiaoxia;Hu, Shuang;Ding, Tingbo;Chen, Yan;Cao, Yang;Mo, Mingguang;Dong, Jibin;Wei, Min;Chu, Yong;Li, Huiti;Jiang, Xian-Cheng;Cheng, Nengneng;Zhou, Lu [European Journal of Medicinal Chemistry,2019,vol. 163,p. 864 - 882] Location in patent:supporting information