Acetic Acid → HCID 67300348, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of NaOH (1.32 g, 33.0 mmol), H2O (8.8 mL), and 1,4 dioxane (2 mL) at ice bath temperature was added Br2 (0.6 mL, 12.3 mmol) and stirred for 5 minutes. The resulting hypobromite solution was added dropwise to a stirred solution of the compound obtained in step II (0.6 g, 2.2 mmol) in 1,4-dioxane (2.4 mL) at around 10° C. The reaction mixture was gradually warmed to r.t, stirred for 1 h, then cooled to 0° C. and quenched by adding acetic acid (2 mL, 36.3 mmol). The mixture was diluted with water and extracted in EtOAc. The combined organic layer was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure to obtain 1-[(tert-butoxycarbonyl)amino]tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (0.54 g) as a viscous liquid in 87% yield. m/z (M−1) 280; 1H NMR (CDCl3) 300 MHz δ 4.75 (s (br), 1H), 2.78-2.60 (m, 1H), 2.47-2.40 (m, 1H), 2.33-2.22 (m, 1H), 2.18-1.72 (m, 8H), 1.62-1.53 (m, 1H), 1.43 (s, 9H).

Provenance & Evidence