Methyl chloroformate → HCID 22141219, compound

Participants

Reaction Steps

A solution of [6-(3-aminophenyl)-3-hexyl-3-azabicyclo[3.1.0]hex-6-yl]methanol (Preparation 94, 0.03 g, 0.09 mmol) in tetrahydrofuran (1 ml) was stirred at 0° C. under an atmosphere of nitrogen. The reaction mixture was treated with triethylamine (0.03 ml, 0.19 mmol) followed by dropwise addition of methyl chloroformate (0.01 ml, 0.17 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h before pouring onto aqueous saturated sodium hydrogen carbonate (50 ml). The product was extracted with ethyl acetate (3×25 ml) and the combined organic extracts were dried (Na2SO4) and then concentrated in vacuo to give a brown residue. The crude product was purified by preparative HPLC (condition 11) to give a clear glass (6 mg, 15% yield).

Provenance & Evidence