N,N,N',N'-Tetramethylethylenediamine → HCID 18340685, compound

Participants

Reaction Steps

Anhydrous EtOAc (0.94 mL, 9.6 mmole) was added dropwise to a solution of lithium bis(trimethylsilyl)amide (1.0 M in THF, 7 mL, 7 mmole) in dry THF (7 mL) in a flame-dried flask at −78° C. under argon. After 0.5 hr, TMEDA (2.4 mL, 16 mmole) was added. After another 5 min, a solution of 3-methoxydibenzo[b,f]oxepin-10-one (760 mg, 3.2 mmole) in THF (2 mL) was added dropwise over 3 min. Additional dry THF (0.4 mL) was used in transfer. The reaction was stirred at −78° C. to −40° C. for 1 hr, then was quenched with saturated NH4Cl (10 mL). The mixture was wanned to RT and extracted with EtOAc. Drying (MgSO4), concentration, and flash chromatography on silica gel (10% EtOAc/hexanes) gave the title compound as a clear oil: 1H NMR (300 MHz, CDCl3) δ1.14-1.20 (t, 3 H), 1.21-1.30 (m, 1 H), 2.62-2.68 (dd, 1 H), 2.94-3.02 (dd, 1 H), 3.24-3.30 (dd, 1 H), 3.40-3.46 (dd, 1 H), 3.40-3.46 (dd, 1 H), 3.78 (s, 3 H), 4.08-4.18 (m, 2 H), 6.60-7.26 (m, 6 H), 7.64-7.68 (dd, 1 H).

Provenance & Evidence