1-Methyl bicyclo[2.2.2]octane-1,4-dicarboxylate

A mixture of the title compound from Step B above (20 g) and KOH (5.5 g) in MeOH/HStep C. A mixture of the title compound from Step B above (20 g) and KOH (5.5 g) in MeOH/H2O (10:1, 106 mL) was heated to reflux overnight, cooled to room temperature and concentrated. The residue was diluted with EtOAc and extracted with IN aqueous NaOH (2 x 10O mL). The organic phase was dried (MgSOTo a mixture of dimethyl bicyclo[2.2.2]octane-l, 4-dicarboxylate (2.0 g, 8.84 mmol) in 10 mL MeOH was added NaOH (0.35 g, 8.8 mmol) and 0.5 mL water. The mixture was stirred at 75 °C for 4 h and at rt for 12 h. The mixture was diluted with water and washed with ΕA solution of dimethyl bicyclo[2.2.2]octane-l, 4-dicarboxylate (58.0 g, 0.25 mol) in methanol (600 mL) was heated under reflux. To this solution was added a solution of potassium hydroxide (9.8 g, 0.175 mol) in methanol (100 mL) and water (12 mL) over 30 minutes. The reaction mixture was refluxed for 24 h. The solvent was then removed and the residue was diluted with water. The aqueous solution was extracted with ethyl acetate (2 x200 mL) to recover starting material (22.0 g), and the aqueous layer was acidified to pH 3 by addition of hydrochloric acid. A precipitate was formed and extracted with ethyl acetate (3 x 300 mL). The combined extracted were washed with brine, dried over sodium sulfate and concentrated to give the titled product (30.0 g, 0.14 mol, 55 percent yield).1H NMR(400 MHz, CDCI3) δ ppm 3.65 (s, 3H), 1.81 (s. 12H); MS (ESI) m/z 211.3 [M-H]Step 3A-10.0 g of a compound represented by the formula (I-70-1), 100 mL of methanol and 7.1 g of a 25percent sodium hydroxide aqueous solution were added to a reaction vessel, and the mixture was stirred at 50 ° C. for 5 hours. Cool and add chloroform. 10percent hydrochloric acid was added to adjust the pH of the aqueous layer to 4 to 5, and liquid separation treatment was carried out. The organic layer was washed with brine and dried over sodium sulfate. Purification by column chromatography (hexane / ethyl acetate) gave 5.6 g of a compound represented by the formula (I-70-2).

Molecular Weight:212.24
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:212.10485899
Monoisotopic Mass:212.10485899
Topological Polar Surface Area:63.6
Heavy Atom Count:15
Complexity:283
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes