Ammonium Acetate → HCID 59192499, compound

Participants

Reaction Steps

To a stirred and ice cold solution of (3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (1.32 g, 4.01 mmol) and ammonium acetate (4.7 g, 61.0 mmol) in methanol (21 mL) was added sodium cyanoborohydride (504 mg, 8.02 mmol) under nitrogen. After 10 minutes of stirring at room temperature, the reaction mixture was heated at reflux for 4 hours. The solvent was removed under reduced pressure and to the residue was added saturated sodium bicarbonate solution (10 mL). The resulting solution was extracted with dichloromethane (25 mL×3). The organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford (5-amino-3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (1.26 g, 98%), which is used in the next step without further purification.

Provenance & Evidence