反应详情

To a solution of 6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-naphtho-[2,3-b][1,4]oxazine-4-carboxylic acid benzyl ester (0.40 g, 1.1 mmol) in THF was added 2.8 ml of LiAlH4 solution (1.0 M) in THF. The resulting solution was stirred at reflux for 3 h. The reaction mixture was quenched with ice, diluted with EtOAc and filtered through Celite. The organic layer was dried over Na2SO4 and concentrated in vacuo, yielding an oily residue which was subjected to column chromatography (5% MeOH-EtOAc) to yield 0.19 g (75%) of the desired product. 1H NMR (300 MHz, CDCl3): δ 2.07 (m, 1H), 2.28 (m, 1H), 2.37 (s, 3H), 2.49 (m, 1H), 2.77 (m, 2H), 2.97 (dd, 1H, J=5.5, 16.1 Hz), 3.28 (dd, 1H, J=5.5, 17.0 Hz), 3.55 (m, 1H), 3.79 (s, 3H), 3.86 (m, 2H), 6.67 (m, 2H), 7.09 (t, 1H, J=7.8 Hz).

1. temperatureat reflux for 3 h
2. customThe reaction mixture was quenched with ice
3. additiondiluted with EtOAc
4. filtrationfiltered through Celite
5. dry with materialThe organic layer was dried over Na2SO4
6. concentrationconcentrated in vacuo
7. customyielding an oily residue which