Potassium Carbonate → HCID 68511182, compound

Participants

Reaction Conditions

Reaction Steps

((S)-5-Bromo-indan-2-yl)-methanol (1.45 g, 6.38 mmol) was dissolved in toluene (12 mL) and argon gas bubbled through the solution for 10 minutes. To the stirring mixture was added, in the following order: tert-butyl carbamate (1.25 g, 10.67 mmol), copper(I) iodide (255 mg, 1.33 mmol), K2 CO3 (2.46 g, 17.8 mmol) and finally N,N′-dimethylethylene-1,2-diamine (285 μL, 2.61 mmol). The mixture was mechanically stirred under argon at 110° C. After 18 hours, tlc monitoring of the reaction showed remaining starting material, the following additional reagents were added: tert-butyl carbamate (125 mg, 1.06 mmol), copper(I) iodide (25 mg, 0.13 mmol), potassium carbonate (250 mg, 1.8 mmol) and N,N′-dimethylethylene-1,2-diamine (30 μL, 0.27 mmol). Heating at 110° C. was continued for 2 hours after which the reaction mixture was cooled, solids removed by filtration and the filtrate evaporated, dissolved in a minimum amount of CH2Cl2 and purified by flash chromatography (ethyl ether). A crude product was obtained which was crystallized from 1:1 diethyl ether:hexane to give ((S)-2-Hydroxymethyl-indan-5-yl)-carbamic acid tert-butyl ester (410 mg, 24%) of white crystals. The mother liquor, comprised of a mixture of desired product and starting material was reserved to be reacted again.

Provenance & Evidence