1: in diethyl ether; dichloromethane T=-48°C; Grignard reaction; 2: With hydrogenchloride in 1,4-dioxane; methanol T=20°C; Substitution; 0.5 h; Solvolysis; Title compound not separated from byproducts;

1: 93 percent / BF3*Et2O / benzene / 4 h / Heating; Cope apparatus (4 Angstroem molecular sieves) 2: n-butyllithium / tetrahydrofuran; hexane / 6 h / -78 °C / other temperature 3: hydroxylamine hydrochloride, AcONa*3H2O / ethanol / 19 h / Ambient temperature 4: dioxane / 4 h / Ambient temperature 5: 10percent HCl-MeOH / Ambient temperature View Scheme

1: n-butyllithium / tetrahydrofuran; hexane / 6 h / -78 °C / other temperature 2: hydroxylamine hydrochloride, AcONa*3H2O / ethanol / 19 h / Ambient temperature 3: dioxane / 4 h / Ambient temperature 4: 10percent HCl-MeOH / Ambient temperature View Scheme

1: hydroxylamine hydrochloride, AcONa*3H2O / ethanol / 19 h / Ambient temperature 2: dioxane / 4 h / Ambient temperature 3: 10percent HCl-MeOH / Ambient temperature View Scheme

hydrogenchloride; potassium hydroxide; (2S)-1-methyl-1-lt;N-(diphenylmethylene)gt;-2-hydroxymethylpyrrolidine hydrazonium iodide; potassium carbonate in dichloromethane 24 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 1.) n-butyllithium, 2.) hydroxylamine hydrochloride, AcONa*3H2O / 1.) THF/n-hexane, -78 deg C, 6 h, 2.) ethanol, RT, 24 h, 3.) dioxane, RT, 21 h 2: 10percent HCl-MeOH / Ambient temperature View Scheme