188798-80-3

Starting with D-alanine, N,N-dibenzyl-D-alanine is generated by reflux reaction with excess benzyl bromide in an alkaline aqueous solution of potassium carbonate and sodium hydroxide (or an ethanol/water mixture) via nucleophilic substitution. Subsequently, the resulting dibenzyl amino acid is reacted with methyl iodide in dimethylformamide (DMF) or esterified in methanol via thionyl chloride (SOCl₂) catalysis to efficiently obtain (R)-methyl 2-(dibenzylamino)propanoate.

[1] PROF. DR. MANFRED T. REETZ   Alfred S  Mark W Drewes. Stereoselective Synthesis of β-Amino Alcohols from Optically Active α-Amino Acids†[J]. Angewandte Chemie International Edition, 1987, 26 11: 1141-1143. DOI:10.1002/anie.198711411.