Benzyl Alcohol → HCID 11810403, compound

Participants

Reaction Steps

Dimethylaminopropylethylcarbodiimide (EDC) (1.68 E, 8.78mmol) was added to a solution of the crude N-Boc-D-Phe (as described previously, assumed to be 7.32 mmol), benzyl alcohol (1.14 ml, 11.0 mmol) and 4-pyrrollidinopyridine (217 mg, 1.46 mmol) in dichloromethane (73.2 ml). The reaction mixture was stirred at room temperature overnight, diluted with dichloromethane, and washed sequentially with a dilute solution of HCl (<5%, pH 3.0), a solution of saturated sodium bicarbonate, and brine. The combined organic layers were dried over MgSO4 and concentrated to obtain a yellow oil. This substance was subjected to silica gel chromatography, eluted with a solution that was 5:1 hexanes:ethyl acetate, and resulted in a yield of 2.31 g of N-Boc-D-Phe-OBn.

Provenance & Evidence