Acetic Acid → 1-Methoxytricyclo[3.3.1.03,7]nonane-3-carboxylic acid

To a mixture of NaOH (5.8 g, 147 mmol), H2O (40.0 mL) and 1,4 dioxane (10 mL) at ice bath temperature was added Br2 (2.8 mL, 55.0 mmol) and stirred for 5 minutes. The resulting hypobromite solution was added drop-wise to a stirred solution of 1-(1-methoxytricyclo[3.3.1.03,7]non-3-yl)ethanone obtained from step III (1.9 g, 9.8 mmol), in 1,4-dioxane (10 mL) at ice bath temperature. The reaction mixture was gradually warmed to room temperature and stirred for 1 h. The reaction mixture was cooled to ice bath temperature and AcOH (3.9 mL, 65.7 mmol) were added. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-methoxytricyclo[3.3.1.03,7]nonane-3-carboxylic acid (1.3 g) in 72% yield. m/z (M+1), 197; 1H NMR (CDCl3) 300 MHz δ 3.30 (s, 3H), 2.78-2.70 (m, 1H), 2.57-2.48 (m, 1H), 2.38-2.28 (m, 1H), 2.11-2.0 (m, 2H), 1.86-1.69 (m, 5H), 1.59-1.51 (m, 2H).

1. stirringstirred for 1 h
2. additionwere added
3. extractionextracted with EtOAc
4. washThe combined organic layer was washed with brine
5. dry with materialdried over Na2SO4
6. customthe solvent was removed under reduced pressure

ORD record

ord-31ad325b92f1483ebab5f6b5a2b402ee

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985759B2