Lithium diisopropylamide → HCID 86655977, compound

Participants

Reaction Conditions

Reaction Steps

2-{Benzyloxycarbonyl-[3-(1(R)-phenyl-ethylimino)-propyl]-amino}-acetic acid ethyl ester (0.909 g; 2.29 mmol) is dissolved in dry THF (20 ml). The reaction mixture is cooled to −78° C. and LDA (1.6 ml of a 2M solution in THF) is added slowly. The reaction mixture is stirred for 6 hours at −78° C. Then, the reaction mixture is poured in chilled saturated aqueous ammonium chloride solution and extracted with ethyl acetate; the phases are separated. The aqueous phase is extracted twice with ethyl acetate (2 times 100 ml). The combined organic phases are washed with water (50 ml) and with brine twice (2 times 50 ml). The organic phase is dried over magnesium sulfate. The solids are filtered off and the solvent is removed under reduced pressure. The crude product is purified by column chromatography over silicagel (eluent: hexane/ethyl acetate 50:1 to 10:1). 0.418 g of a colorless yellow oil (yield 52%) are obtained.

Provenance & Evidence