[BH4-].[Na+].[N:3]1([C:9]2[CH:10]=[C:11]([OH:17])[C:12](=[CH:15][CH:16]=2)[CH:13]=[O:14])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.CC(C)=O.Cl>O>[OH:14][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][CH2:8]2)=[CH:10][C:11]=1[OH:17]
A solution of sodium borohydride (NaBH4) (0.66 g, 17 mmol) in water (25 mL) was treated with 4-morpholinylsalicylaldehyde (1.8 g, 9 mmol) in small portions over 30 min and stirred at room temperature for 3 h. The reaction was quenched with acetone (5.1 mL, 100 mmol), acidified to pH 7 with 7.8 mL of 5% hydrochloric acid (aqueous) and extracted with chloroform (CHCl3) (2×100 mL). The combined CHCl3 extracts were dried over sodium sulfate (Na2SO4) and concentrated in vacuo to yield 0.7 g of pale yellow solid which was purified by trituration with 60/40 CHCl3/ethyl acetate (EtOAc) to yield the product as a white solid (0.25 g).
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