N,N,N',N'-Tetramethylethylenediamine → HCID 66977049, compound

Participants

Reaction Conditions

Reaction Steps

LHMDS (1M THF solution; 2.4 mL, 2.4 mmol) was added to a −78° C. solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (514 mg, 2 mmol) in anhydrous THF (5 mL) and the reaction was allowed to warm to 0° C. over the course of 30 mins, whilst under an inert atmosphere. This solution was added drop-wise to a solution of allylpalladium chloride dimer (365 mg, 1 mmol), TMEDA (302 uL, 2 mmol) in anhyrdous THF (2.5 mL) in an oven dried flask under an inert atmosphere at −60° C. A balloon of carbon monoxide was attached and the reaction stirred for 2.5 h at 0° C. Saturated ammonium chloride solution (10 mL) was added, the reaction mixture extracted with Et2O (20 mL) and the organic phase washed with sat. brine (20 mL), dried (MgSO4) and concentrated in vacuo. The desired product was isolated as an oil by normal phase chromatography (Grace 12 g, 25-75% hexane:EtOAc, gradient elution; visualised with permangenate stain) (164 mg, 28% yield). 1H NMR (CDCl3) δ 4.16 (q, J=7.1 Hz, 2H), 4.08-3.84 (m, 2H), 2.72 (s, 2H), 1.99 (dd, J=13.5, 2.0 Hz, 2H), 1.43 (s, 9H), 1.33-1.16 (m, 5H), 0.91 (tt, J=8.1, 5.8 Hz, 1H), 0.41-0.26 (m, 4H).

Provenance & Evidence