Benzyl Alcohol → BOC-L-Alanine benzyl ester

Participants

Reaction Conditions

Reaction Steps

N2-(tert-Butoxycarbonyl)-L-alanine (1.13 g, 5.83 mmol) is dissolved in dry DCM (6 ml), some 3 Å molecular sieves are added, and the mixture is then cooled to 0° C. Benzyl alcohol (1.81 ml, 17.48 mmol, 3 equivalents), EDCI (2.23 g, 11.65 mmol, 2 equivalents), and DMAP (71 mg, 0.58 mmol, 0.1 equivalent) are added. The mixture is stirred for 150 min, during which it is allowed to slowly warm to RT. The mixture is then concentrated to dryness and the residue is worked up by chromatography (Biotage, cyclohexane-ethyl acetate 9:1). Product-containing fractions are combined and concentrated. The title compound is obtained in a yield of 1.03 g (63% of theory).

Provenance & Evidence