Ethylene Oxide → 7-(2-Hydroxy-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

Participants

Reaction Conditions

Reaction Steps

To 1.80 g (5.00 mmol) 7-iodo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (preparation 7b) in 5.0 mL THF at −20° C. is added 6.34 g (5.50 mmol) of a THF-solution of 14% isopropylmagnesium-chloride*lithiumchloride under argon. The mixture is warmed to 0° C. and stirred 1 h at 0° C. The reaction mixture is cooled to −60° C. and 0.88 g (20.0 mmol) oxirane in 2.0 mL THF is added. The cooling bath is removed and the reaction is warmed to RT. The reaction mixture is poured into 50 mL aqueous ammonium chloride solution and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with water, dried over MgSO4. After filtration and evaporation of the solvent, the residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95).

Provenance & Evidence