Sodium borohydride → HCID 18516204, compound

Participants

Reaction Steps

To a stirred solution of NaBH4 (0.18 g, 4.89 mmol) in anhydrous 50% MeOH/THF at 0° C. was added powdered CaCl2 (0.54 g, 4.89 mmol). The suspension was stirred 20 minutes and a solution of Example 237D (0.50 g, 1.63 mmol) in anhydrous 50% MeOH/THF was slowly added over a period of 10 minutes. The reaction stirred 1 hour at 0° C. followed by 16 hours at room temperature. Reaction was quenched into a slurry of dilute AcOH (aq)/ice. After all gas evolution ceased with occasional stirring, aqueous was made basic with sat. NaHCO3. Aqueous was extracted with dichloromethane (3×40 mL) and extracts combined. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel using EtOAc/hexane as eluent to provide dimethylethyl 4-(hydroxymethyl)-thieno[2,3-c]pyridine-2-carboxylate compound as a solid (0.14 g, 32%).

Provenance & Evidence