反应详情

To the 8 L of 1:1 methanol/water mixture containing the resultant compound from Example 1C was added 60 g of W-24 raney nickel. The resulting suspension was pressurized under 50 psi of hydrogen and was allowed to shake on a Parr shaker for 24 hours, at which time an additional 20 g of raney nickel catalyst was added. After 6 hours under 50 psi of hydrogen, the catalyst was removed by filtration and the solution was concentrated to dryness. To the dry white solid, ethyl acetate (6 L) and heptane (4 L) were added and the solution was vigorously stirred with a mechanical stirrer overnight. The white suspended solid was removed by filtration yielding 530 g (88%) of the desired product as an amorphous powder that was contaminated with approximately one equivalent of sodium bromide. The compound was used without any additional purification: IR (KBr) 1740, 1215, 1050 cm-1. 1H NMR (DMSO-d6, 300 MHz) δ 2.48-2.54 (m, 1H), 2.74-2.87 (m, 2H), 2.91-3.04 (m, 2H), 3.48 (s, 3H), 7.12-7.32 (m, 5H); 13C NMR (75 MHz, D2O/DMSO-d6) δ 38.18, 44.80, 52.67, 52.82, 127.42, 129.13, 129.34, 138.14, 176.84.

1. customthe catalyst was removed by filtration
2. concentrationthe solution was concentrated to dryness
3. additionTo the dry white solid, ethyl acetate (6 L) and heptane (4 L) were added
4. customwas removed by filtration