Acetone → HCID 131729256, compound

Participants

Reaction Steps

Dissolve 5-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (1.0 g, 2.26 mmol) and acetone (250 μL, 3.39 mmol) in dry 1,2-dichloroethane. Add sodium triacetoxyborohydride (1.0 g, 4.53 mmol) and stir overnight at room temperature. Add 1 N NaOH solution to the reaction mixture and extract with CH2Cl2 (2×25 mL). Combine the organic portions and wash with water (2×25 mL). Dry the organic layer with Na2SO4, then filter, and concentrate in vacuo. Triturate the crude yellow solid with Et2O and filter. Wash the solid with Et2O several times and re-dissolve in CHCl3. Add 1 N HCl/Et2O solution (1.5 mL) and remove the solvent in vacuo to give 630 mg (53%) of the title compound. ES/MS m/z (35Cl) 484.2 [M+1]+.

Provenance & Evidence