Nitrogen → HCID 89813373, compound

Participants

Reaction Conditions

Reaction Steps

Add potassium hydride (30%, 2.6 g, 19.4 mmol) portion wise under N2 to a cooled solution (0° C.) of 4-(dibenzylamino)-2-methylbutan-2-ol (5 g, 17.6 mmol) in THF (50 mL). Stir the mixture at 0° C. for 0.5 h, treat with MeI (2.76 g, 19.4 mmol) dropwise, allow the mixture to warm to RT and stir for 3 h. Re-cool the mixture to 0° C., treat with saturated. NH4Cl, and remove the organics under reduced pressure. Extract the residue with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography (Pet ether/EtOAc, 50:1) to afford the title compound (3.0 g, 57% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.29 (m, 10H), 3.58 (s, 4H), 3.05 (s, 3H), 2.50 (m, 2H), 1.73 (m, 2H), 1.07 (s, 6H).

Provenance & Evidence