Potassium Carbonate → 5-[2-(Tert-butoxycarbonyl-methyl-amino)-propyl]-benzo[1,3]dioxole-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To 2.5 g (8.8 mmol) of 1C was added 20 mL of anhydrous N, N-dimethylformamide (DMF) followed by 3.68 g (26 mmol) of anhydrous K2CO3 and 3 mL (23 mmol) of ethyl dibromoacetate. The reaction mixture was heated to 100° C. for 4.5 hours and then allowed to cool to room temperature. This was concentrated to dryness under reduced pressure, and 50 mL of water was added to the residue. The mixture was adjusted to pH 3 using 1N HCl and extracted with 4×50 mL of dichloromethane. Organic layers were combined, dried (anhydrous Na2SO4), and concentrated to dryness. The residue was purified by flash column silica gel chromatography using 15% ethyl acetate in hexane to give 1.1 g (3.01 mmol, 34%) of 1D as a colorless oil (M+Na, 388).

Provenance & Evidence