Acetic Acid → Acetic acid 3-benzyl-3-aza-bicyclo[3.2.1]oct-6-yl ester

Participants

Reaction Steps

To the above solution of acetic acid 2,4-diformyl-cyclopentyl ester was added at room temperature benzyl amine (5.8 mmol) and acetic acid (5.8 mmol) under nitrogen. After 2 h at room temperature sodium triacetoxy borohydride (25 mmol) was added and the reaction mixture was allowed to stir at room temperature for 18 h. The reaction mixture was quenched by the addition of saturated sodium bicarbonate solution (100 mL) and the phases were separated. The aqueous layer was extracted with dichloromethane (3×100 mL). The solvents were removed via rotary evaporation and the residue was purified by silica gel chromatography to afford a yellow oil (3.6 mmol). 1H NMR (CDCl3, 400 MHz): δ 7.37 (m, 2H), 7.23 (m, 3H), 5.15–4.95 (m, 1H), 3.63–3.35 (m, 2H), 2.84–2.55 (m, 2H), 2.25–2.15 (m, 4H), 2.08 (s, 3H), 1.80–1.70 (m, 2H), 1.62–1.25 (m, 2H); APCl MS m/z 260.2 (M+H)+.

Provenance & Evidence