N,N-dibenzyl-3-methoxy-3-methylbutan-1-amine

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add potassium hydride (30%, 2.6 g, 19.4 mmol) portion wise under N2 to a 0° C. solution 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 drop-wise with methyl iodide [MeI] (2.76 g, 19.4 mmol), 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%). 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). treat to warm to RT stir for 3 h remove the organics under reduced pressure Extract the residue with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate purify via silica gel chromatography (Pet ether/EtOAc, 50:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). to warm to RT 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 purify via silica gel chromatography (Pet ether/EtOAc, 50:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add potassium hydride (30%, 2.6 g, 19.4 mmol) portion wise under N2 to a 0° C. solution 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 drop-wise with methyl iodide [MeI] (2.76 g, 19.4 mmol), 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%). 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). treat to warm to RT stir for 3 h remove the organics under reduced pressure Extract the residue with EtOAc (3×) wash the combined organics with brine dry over Na2SO4 concentrate purify via silica gel chromatography (Pet ether/EtOAc, 50:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). to warm to RT 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 purify via silica gel chromatography (Pet ether/EtOAc, 50:1)