Potassium Hydroxide → HCID 86681850, compound

Participants

Reaction Steps

To a stirred solution of 4-(2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butan-1-ol (step 3) (50 mg, 0.139 mmol) in toluene (1 ml) was added KOH (40% aq, 1 ml, 0.139 mmol) and tetrabutylammonium hydrogen sulfate (47.2 mg, 0.139 mmol) followed after 5 min at RT, by tertiary butyl bromoacetate (90 uL). The reaction mixture was stirred at RT for 24 h. The mixture was diluted with ether and the phases were separated. The aqueous portion was extracted with ether (×2), the combined organics were dried (sodium sulphate), filtered and the solvent removed in vacuo. The residue was dissolved in THF (1 ml) followed by the addition of KOH (40% aq, 1 ml, 0.139 mmol), tetrabutylammonium hydrogen sulfate (47.2 mg, 0.139 mmol) and tertiary butyl bromoacetate (88 uL). The reaction mixture was stirred at RT for 6 h. The mixture was diluted with ether and stirred at RT for 12 h. The phases were separated, the aqueous extracted with ether (×2), the combined organics were dried (sodium sulphate), filtered and the solvent removed in vacuo. The crude material was purified on silica eluting with 0-100% EtOAc/DCM to afford the title compound:

Provenance & Evidence