Methyl iodide → HCID 22335621, compound

Participants

Reaction Steps

4-[2-(4-Fluorophenyl)-3-methoxycarbonyl-6,7-dihydro-5H-pyrrolizin-1-yl]benzenesulphonyl chloride (1.7 g, 3.8 mmol), suspended in water (10 ml), is treated with Na2SO3 (0.56 g, 4.4 mmol) and then with Na2CO3 (0.72 g, 6.8 mmol) and stirred at 70° C. for 2 h. The solution is treated with a solution of CH3I (0.88 g, 6.2 mmol) in ethanol (20 ml) and heated under reflux for 2 h. After cooling, the ethanol is removed in vacuo, the residue is treated with water (25 ml) and the product from the reaction is taken up in ethyl acetate (2×30 ml). The ethyl acetate phase is washed with conc. NaCl solution and water, dried using Na2SO4 sicc. and the filtrate is concentrated. After removing the solvent in vacuo, 0.4 g (25%) of methyl 2-(4-fluorophenyl)-1-(4-methylsulphonylphenyl)-6,7-dihydro-5H-pyrrolizine-3-carboxylate remains as a residue having a concentration of 77%.

Provenance & Evidence