Diisopropylamine → HCID 67518348, compound

Participants

Reaction Steps

A solution of tert-butyl{4-(2-bromoethyl)-6-[(2,2-dimethylpropanoyl)amino]pyridin-3-yl}acetate (6.5 g, 16.3 mmol) in tetrahydrofuran (50 mL) cooled in a dry ice-acetone bath was treated with a solution of lithium diisopropylamide in tetrahydrofuran (50 mL) (prepared from diisopropylamine (3.79 g, 34.7 mmol) and n-butyllithium (2.5 M, 13.7 mL) dropwise via addition funnel over 1 h. After complete addition, the reaction stirred an additional 1 h, then was quenched with saturated sodium bicarbonate solution and allowed to warm to room temperature. The resulting mixture was diluted with ethyl acetate and water and transferred to a reparatory funnel. The layers were separated and the aqueous extracted with ethyl acetate (2×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the resulting residue (2−>25% EtOAc/hexanes eluent) provided tert-butyl 3-[(2,2-dimethylpropanoyl)amino]-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylate. 1H NMR (500 MHz, CDCl3), δ 8.27 (s, 1H), 8.16 (s, 1H), 8.06 (br s, 1H), 3.96 (dd, J=5.0, 5.5 Hz, 1H), 3.06 (m, 1H), 2.90 (m, 1H), 2.45 (m, 1H), 2.32 (m, 1H)-1), 1.47 (s, 9H), 1.32 (s, 9H); LC/MS (M+1)+=319.0;

Provenance & Evidence