반응 #2296779

반응 방정식

1-(2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylcarbonyl)piperidin-4-ol

lithium aluminum hydride

→

title compound

수율 92.5%

1-(2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)-piperidin-4-ol

수율 92.5%

용매

diethyl ether

반응 조건

후처리

1. 1
   온도warmed to room temperature
2. 2
   workup.WAITAfter 18 h at room temperature
3. 3
   기타the excess reagent was carefully quenched with the following in sequence
4. 4
   workup.STIRRINGThe suspension was stirred vigorously until the aluminum salts
5. 5
   workup.ADDITIONThe suspension was diluted with ethyl acetate (100 mL)
6. 6
   건조dried with a small amount of anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   세척The filter cake was rinsed thoroughly with ethyl acetate
9. 9
   기타The solvent was removed

실험 절차

To a cooled suspension (0° C.) of 1-(2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylcarbonyl)piperidin-4-ol (described in Example 82a) (6.95 g, 19.6 mmol) in diethyl ether (200 mL) under nitrogen was added lithium aluminum hydride (1.49 g, 39.2 mmol, 8 eq of hydride) in portions. The suspension was stirred at 0° C. for 30 min and warmed to room temperature. After 18 h at room temperature, the excess reagent was carefully quenched with the following in sequence: water (1.5 mL), 2.5 N NaOH (1.5 mL) and additional water (4.5 mL). The suspension was stirred vigorously until the aluminum salts became a granular white solid. The suspension was diluted with ethyl acetate (100 mL), dried with a small amount of anhydrous magnesium sulfate and filtered. The filter cake was rinsed thoroughly with ethyl acetate. The solvent was removed to yield 6.16 g (92%) of the title compound as a white solid. No additional purification was required. TLC analysis (Rf 0.15, 50% ethyl acetate in hexane). NMR (CDCl3, 300 MHz) 7.20 (m, 4H), 6.95 (m, 3H), 4.60 (s, 1H), 4.24 (s, 1H), 3.70 (m, 1H), 3.34 (s, 2H), 2.88 (m, 2H), 2.58 (s, 2H), 2.37 (m, 2H), 1.57 (m, 2H) MS (CI, CH4) m/z 340 (M+1.98), 342 (33), 322 (100), 368 c(M+29,22), 114 (26)

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