Ethanol → HCID 58276247, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl {2-[(3′-cyano-4-biphenyl)oxy]ethyl}(4,4-dimethylcyclohexyl)carbamate (0.125 g; 0.279 mmol; step 1 above) in EtOH (2.5 mL) at room temperature was added a solution of hydroxylamine (0.25 mL of a 50 wt % aq solution). The mixture was stirred 70 h at room temperature and volatiles were removed in vacuo (1×PhMe chase). The residue was dissolved in trimethyl orthoformate (2 mL), TsOH.H2O (0.0025 g; 0.013 mmol) was added and the mixture was heated at 100° C. in a sealed vial for 1 h. Upon cooling, the mixture was adsorbed onto a small amount of silica gel and purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum. LC/MS (method A) tR 3.34 min, m/z 492 (M+H, 5%), 514 (M+Na, 100%), 392 ([M-Boc]+H, 53%).

Provenance & Evidence