1.1: potassium iodide / 1-methyl-pyrrolidin-2-one / 26 h / 120 °C 2.1: lithium borohydride / tetrahydrofuran / 18 h / 0 °C 2.2: 1 h 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 1 h / -78 - 20 °C / Inert atmosphere 4.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran / 21 h / 45 °C 5.1: sodium methylate / methanol / 1 h / Inert atmosphere 6.1: water; sodium hydroxide / acetone / 0.08 h 7.1: β-glucuronidase solution / 0.5 h / 37 °C / pH 6.8 / Phosphate buffer View Scheme

dihydrogen peroxide; isopentyl nitrite 1.) ethyl acetate, 50 deg C, 5 h 2.) 100 deg C, glacial acetic acid; Yield given. Multistep reaction. Yields of byproduct given;