Tetrahydrofuran → HCID 68869448, compound

Participants

Reaction Conditions

Reaction Steps

NaH (55 mg, 1.31 mmol, 60% by wt suspension in mineral oil) was added at 0° C. to a solution of [2-(3′-Chloro-4′-fluoro-biphenyl-4-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (0.5 g, 1.31 mmol) in 5 mL anhydrous THF and stirred for 20 min at 0° C. Mel (0.37 g, 2.63 mmol) was added to the reaction mixture and stirred for 6 h at room temperature. The reaction mixture was diluted with 5 mL EtOAc, and washed with water, brine and dried over Na2SO4. Solvent was removed under vacuum and silica gel chromatography (EtOAc: Hexanes) gave (R)-[[2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-methoxymethyl-ethyl]-carbamic acid tert-butyl ester (0.38 g). The Boc protecting group was removed by stirring the compound in 4M HCl in dioxane (5 ml) for 30 min. Evaporation of the solvent under vacuo gave (R)-2-(3′-chloro4′-fluoro-biphenyl-4-yl)-1-methoxymethyl-ethylamine hydrochloride.

Provenance & Evidence