Ammonium Chloride → 3(S)-(6-Amino-pyridin-3-yl)-3-[benzyl-(1(R)-phenylethyl)-amino]-propionic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of (R)-(+)—N-benzyl-α-methylbenzylamine (4.0 g, 19 mmol) in 50 mL THF was gradually added n-butyllithium (11.3 mL, 2.5 M, 28.2 mmol) over 5 min. The mixture was stirred for 30 min at 0° C. and cooled to −78 ° C. A solution of 10-2 (2.0 g, 9.4 mmol) in 20 mL THF was gradually added. After stirring for 40 min at −78° C., it was treated with NH4Cl (sat.) at −78° C., warmed to room temperature and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After solvent evaporation, the residue was purified using silica gel flash chromatography (EtOAc/hexanes 1:2) to afford the desired product 10-3 as an oil.

Provenance & Evidence