[NH2:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][CH:13]=[O:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[BH4-].[Na+].CC(C)=O>O1CCCC1.CC(O)C.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:11][CH2:12][CH2:13][OH:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]A solution of aldehyde 80 (253 mg, 1.3 mmol) in tetrahydrofurane (1 mL) and propan-2-ol (2 mL) was treated with solid sodium borohydride (175 mg, 4.6 mmol) and stirred at −5° C. for 15 min. Acetone (5 mL) was added, stirred at the same temperature for 10 min and then diluted with ethyl acetate (100 mL), washed with 5% KHSO4 in water, then saturated NaHCO3 and finally with water, dried (MgSO4), and used for the next step without further purification.
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