Benzaldehyde → N-Benzyl-L-proline ethyl ester

Participants

Reaction Steps

Into a 500 ml 3-necked roundbottom flask, was placed ethyl prolinate (20.0 g, 140. mmol). This was followed by the addition of a solution of benzaldehyde (14.8 g, 140. mmol) in dichloromethane (100 ml). This was followed by the addition of a solution of sodium triacetoxyborohydride (60.0 g, 280. mmol) in acetic acid (20 ml). The resulting solution was allowed to stirring for 12 hours at room temperature. Adjustment of the pH to 7 was accomplished by the addition of solid potassium carbonate. The resulting solution was extracted one time with 500 ml of EtOAc and concentrated by evaporation to afford ethyl 1-benzylprolinate that was used without further purification.

Provenance & Evidence