Aluminium lithium hydride → 1-(2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidin-4-ol

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)

1. temperaturewarmed to room temperature
2. waitAfter 18 h at room temperature
3. customthe excess reagent was carefully quenched with the following in sequence
4. stirringThe suspension was stirred vigorously until the aluminum salts
5. additionThe suspension was diluted with ethyl acetate (100 mL)
6. dry with materialdried with a small amount of anhydrous magnesium sulfate
7. filtrationfiltered
8. washThe filter cake was rinsed thoroughly with ethyl acetate
9. customThe solvent was removed

ORD record

ord-eb591786ded545e18b22cafadf2a3d37

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05455246