5-[(2-(3-Phenylpropionyl)-5-pyridyl)methylene]thiazolidine-2,4-dione → 5-[(2-(3-Phenyl-1-hydroxypropyl)-5-pyridyl)methyl]thiazolidine-2,4-dione

Participants

Reaction Steps

To a solution of the title product of Example 67 (260 mg, 0.77 mmol) in methanol (10 ml) was added 3% sodium amalgam (4 g) and the reaction was stirred for 4 hours. The methanol was decanted, evaporated and the resultant solid diluted with water (10 ml). The aqueous solution was adjusted to pH 2 with 1N HCl and extracted with CH2Cl2 (3×10 ml) which was discarded. After neutralization of the aqueous layer to pH 7 with NaHCO3, it was then re-extracted with CH2Cl2 (3×10 ml). These combined organic layers were dried (MgSO4), filtered and concentrated to afford the desired product (94 mg, 36%) isolated as a foam.

Provenance & Evidence