Toluene → HCID 57989160, compound

Participants

Reaction Steps

A solution of (R)-tert-butyl 1-(3-(hydroxymethyl)phenyl)propan-2-ylcarbamate (Example 276, step d) (0.78 g) in dichloromethane (20 mL) was treated with trifluoroacetic acid (5 mL) and stirred at room temperature for 40 minutes. Toluene was added and the solution was concentrated in vacuo. The residue was partitioned between 1M aqueous NaOH and DCM and the phases separated. The aqueous phase was extracted twice more with DCM, then the combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford (R)-(3-(2-aminopropyl)phenyl)methanol as a colourless oil that slowly crystallised to a white solid on standing (0.442 g). A mixture of (R)-(3-(2-aminopropyl)phenyl)methanol (0.223 g), (R)-8-(benzyloxy)-5-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)quinolin-2(1H)-one (0.72 g), sodium iodide (0.219 g) and Hunig's Base (0.77 mL) in acetonitrile (3 mL) was heated at reflux under nitrogen overnight. More (R)-(3-(2-aminopropyl)phenyl)methanol (0.219 g), Hunig's Base (0.51 mL) and acetonitrile (2 mL) were added and the mixture was heated at reflux over a second night. The cooled reaction mixture was diluted with ethyl acetate, washed twice with water, once with brine, then dried (MgSO4) and concentrated onto flash silica in vacuo. The resulting powder was purified by flash chromatography on silica eluting with 5% triethylamine in ethyl acetate to afford the subtitled compound as a pale yellow foam. Yield 0.525 g.

Provenance & Evidence