Cyclobutanol → HCID 131731327, compound

Participants

Reaction Steps

(cis)-1-Acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 4) (200 mg, 0.706 mmol) was dissolved in dichloromethane (DCM) (5 mL), mixed with DIPEA (0.370 mL, 2.119 mmol) followed by 4-nitrophenyl chloridocarbonate (157 mg, 0.777 mmol, available from Fluka) and stirred under nitrogen. Cyclobutanol (0.082 mL, 1.059 mmol) was added after 1.75 hours. The reaction was allowed to stir under nitrogen for 17 hours. The reaction was partitioned between distilled water (20 mL) and EtOAc (60 mL). The aqueous layer was extracted with EtOAc (60 mL) and the organic fractions were combined, washed (brine (50 mL)), dried (sodium sulfate) and evaporated to dryness to give a yellow solid (346 mg). The residue was purified by SP4 on a 25+M Biotage silica column, eluting with a gradient of 0 to 50% ethyl acetate in cyclohexane. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (39 mg). LCMS (Method C): Rt=1.05, MH+=383

Provenance & Evidence