2-amino-3-(4-iodophenyl)propan-1-ol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 12.0 g (43.3 mmol) 2-amino-3-(4-iodophenyl)-propan-1-ol (I41) and 350 mL THF is cooled down to 0° C. 3.81 g (95 mmol) NAH (60% in min. oil) are carefully added and the mixture is stirred at 0° C. for 30 min. 3.25 mL (52.0 mmol) iodomethane are added and cooling is removed. The reaction mixture is stirred at r.t. for 1 h. The mixture is poured onto water and extracted with EtOAc (2×). The combined organic layers are washed with brine, dried with Na2SO4 and the solvent is removed in vacuo. The compound is used without further purification. 3.81 g (95 mmol) NAH (60% in min. oil) are carefully added cooling is removed The reaction mixture is stirred at r.t. for 1 h The mixture is poured onto water extracted with EtOAc (2×) The combined organic layers are washed with brine dried with Na2SO4 the solvent is removed in vacuo The compound is used without further purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 28.5 g (75.0 mmol) 2-amino-3-(4-iodophenyl)propanoate hydrochloride in 300 mL ethanol and 300 mL water is added to a mixture of 14.2 g (375 mmol) NaBH4 and 600 mL water (gas evolution!) and the resulting mixture is stirred at reflux for 2 h. The ethanol is evaporated in vacuo and the remaining aq. Phase is extracted with DCM (4×). The combined organic layers are dried with Na2SO4 and the solvent is removed in vacuo. The compound is used without further purification. at reflux for 2 h The ethanol is evaporated in vacuo the remaining aq. Phase is extracted with DCM (4×) The combined organic layers are dried with Na2SO4 the solvent is removed in vacuo The compound is used without further purification