Diisopropylamine → HCID 54328520, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere were combined diisopropylamine (2.72 ml, 6.79 mmol) and anhydrous THF (30 mls), and the solution was cooled to -78° C. 2.5M butyl lithium (2.72 ml, 6.79 mmol) was added and the solution was allowed to warm to about 3-furan-3-yl-2-pyridin4-ylmethyl propionic acid ethyl ester (2.20 g (80% pure), 6.79 mmol) was added dropwise and the solution was stirred at -78° C. for 1 hour. To this solution was added 1.85 g (6.79 mmol) of N-adamantyl-1-yl-2-bromo-acetamide at -78° C. and the mixture was kept at -78° C. for 16 hours and then warmed to room temperature for 3 hours. The standard reaction workup after silica gel chromatography (1:1 EtOAC:hexane) provided 300 mg of the title compound.

Provenance & Evidence