Acetic Acid → 1-(2-Oxopyrrolidin-1-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid

Participants

Reaction Steps

To a stirred mixture of NaOH (2.4 g, 60.6 mmol), H2O (16 mL) and 1,4 dioxane (4 mL) at ice bath temperature was added Br2 (1.13 mL, 22.6 mmol) and stirred for 5 minutes. The resulting hypobromite solution was added dropwise to a stirred solution of the compound obtained in step I (1.0 g, 4.04 mmol) in 1,4-dioxane (18 mL) at 10° C. The temperature of the reaction was brought to room temperature and the reaction mixture was stirred for 1 h. Then it was cooled to ice bath temperature and quenched by adding acetic acid (3.9 mL, 65.7 mmol). The reaction mixture was diluted with water, extracted with EtOAc, and the combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure to obtain 1-(2-oxopyrrolidin-1-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid as a viscous liquid (1.3 g) in 100% yield. m/z (M+1) 250; 1H NMR (CDCl3) 300 MHz δ 3.42 (t, J=7.0 Hz, 2H), 2.78-2.71 (m, 1H), 2.47-2.23 (m, 6H), 2.08-1.90 (m, 6H), 1.85-1.72 (m, 2H), 1.62 (dd, J=2.4, 11.0 Hz, 1H).

Provenance & Evidence