Lithium Hexamethyldisilazide → HCID 68800867, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried flask under N2, 3-(pyridin-3-ylmethyl)pyridine (0.072 g, 0.42 mmol) was dissolved in THF (3 mL). The solution was cooled to 0° C. Lithium bis(trimethylsilyl)-amide (1 M solution in THF, 0.465 mL, 0.47 mmol) was slowly added and the reaction was stirred at 0° C. for 15 min. The reaction became dark red. A solution of N-(diphenylmethylene)-2-methylpropane-2-sulfinamide (0.121 g, 0.42 mmol) in THF (1 mL) was slowly added drop-wise. The reaction was stirred at 0° C. for 1 hr then removed from the ice bath. Sat. aq. NH4Cl (20 mL) was added and the reaction was stirred vigorously. The product was extracted with EtOAc (3×50 mL). The combined organics were dried over Na2SO4, filtered and concentrated to afford an oil which was purified by flash column chromatography (0-5% MeOH/CH2Cl2). The fractions were combined and concentrated in vacuo to afford the title compound as a white solid. (S) Enantiomer at Sulfur: 1H NMR (CD3OD) δ 8.49 (d, 1H, J=2.20 Hz), 8.46 (dd, 1H, J=1.46 Hz), 8.36 (dd, 1H, J=5.37 Hz), 8.30 (d, 1H, J=2.20 Hz), 7.49-7.33 (m, 11H), 7.25-7.23 (m, 3H), 5.78 (s, 1H), 1.08 (s, 1H ). HRMS m/z (M+H) found: 478.1920 (M+Na).

Provenance & Evidence