Diisopropylethylamine → HCID 59314241, compound

Participants

Reaction Steps

A 100 mL round bottom flask is charged with 2-amino-indane-2-carboxylic acid ethyl ester (750 mg, 3.65 mmol) and dry DCM (10 mL). A stirring bar is added and stirring is initiated. The HBTU (1.38 g, 3.65 mmol) is added. After 2 min, the 2-methyl-3-methoxy-benzoic acid (0.61 g, 3.65 mmol) and DIPEA (1.5 mL, 8.6 mmol) are added. The reaction is allowed to stir for 36 h. Analysis by tlc of the reaction mixture (silica, 50% EtOAc/heptanes) indicates complete consumption of the starting amine. The contents of the reaction flask are diluted with EtOAc (50 mL) and transferred to a separatory funnel. This is washed consecutively with dilute aqueous NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 1.1 g of thick brownish gum. This material is purified utilizing an ISCO Companion with a 40 g cartridge of silica. The gradient is 15% EtOAc in heptanes over 2 column volumes followed by a step gradient to 30% EtOAc then 50% and then 70% EtOAc for 3 column volumes each with ramp of 1 column volume. 35 mL fractions are collected. Fractions 15 through 21 are combined and evaporated in vacuo. Pumping to a constant weight gives a white solid (1.15 g).

Provenance & Evidence