HCID 15453674, compound → HCID 54114465, compound

Participants

Reaction Steps

A 1000 mL 3-neck round bottom flask fitted with a mechanical stirrer, reflux condenser, addition port, and nitrogen inlet was charged with a 1.0 M solution of lithium aluminum hydride (200 mL) in THF and anhydrous THF (200 mL). The solution was cooled in an ice/water bath and 2(R)-amino-3-(4-fluorobenzylsulfanyl)-propionic acid (24.08 g) was added with rapid stirring in small portions over 15 min. The ice bath was removed and the reaction mixture was heated to reflux overnight. After cooling the reaction mixture to room temperature, saturated aqueous potassium carbonate (50 mL) was added dropwise over 1 h. The solids were filtered off and the filter cake was washed with THF. The combined filtrate was dried over anhydrous MgSO4 and concentrated to give 2(R)-amino-3-(4-fluoro-benzylsulfanyl)-propan-1-ol (16.16 g) as a pale amber resin.

Provenance & Evidence