B.CSC.[CH2:5]([O:7][C:8](=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH:17]=O)[CH:11]=1)[CH3:6].Cl>C1COCC1>[CH2:5]([O:7][C:8](=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH3:17])[CH:11]=1)[CH3:6]A solution of borane-dimethylsulphide complex (2M in THF; 20 mL) was added to an ice cold solution of 3-(formylamino)phenylacetic acid ethyl ester (4.1 g; 0.02 mol; from step (i) above) in THF (dry; 100 mL) and the reaction mixture was stirred for 1 hour. The resultant solution was poured onto diluted HCl and the mixture left for 15 minutes, whereafter it was washed with ether to remove unreacted material. The aqueous solution was made alkaline (NaHCO3) and extracted with ether (3 times). The combined organic phases were washed with water, dried (Na2SO4) and evaporated to yield 3.0 g (78%) of the sub-title compound.
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