[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH2:11][CH2:12][CH3:13])[CH:3]=1.[C:14]([OH:17])(=O)[CH3:15].[C:18]([BH3-])#[N:19].[Na+].O.CN(C)[CH:25]=[O:26]>>[CH2:14]([O:17][C:25](=[O:26])[CH2:6][C:5]1[CH:8]=[CH:9][C:18]([NH:19][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([I:1])=[CH:3][C:4]=2[O:10][CH2:11][CH2:12][CH3:13])=[CH:3][CH:4]=1)[CH3:15]1.50 g (5.17 mmol, 1 eq) of 4-iodo-2-propoxybenzaldehyde in solution in 40 ml of dimethylformamide supplemented with 1% of acetic acid is added to a solution in 40 ml of dimethylformamide supplemented with 1% of acetic acid. The reaction mixture is stirred overnight at room temperature. 50 g (5.17 mmol, 1 eq) of sodium cyanoborohydride are added. The reaction medium is heated at 60° C. for 4 hours. After returning to room temperature, the reaction medium is supplemented with water and then extracted with ether. The organic phase is dried over magnesium sulfate, filtered and then concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate 80/20). 2.00 g (85%) of the expected compound are obtained.
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