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

HRID 1490182Notes

Reaction equation

HRID 1490182 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([C:17]([N:19]4[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]4)=O)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([CH2:17][N:19]4[CH2:20][CH2:21][CH:22]([OH:25])[CH2:23][CH2:24]4)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 214806421-(2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylcarbonyl)piperidin-4-ol

Product 1

HCID 214806821-(2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidin-4-olYield 92.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled suspension (0° C.) of 1-(2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylcarbonyl)piperidin-4-ol (described in example 1k) (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), 2.5N 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). 1H 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), 1.85 (m, 2H), 1.57 (m, 2H) MS (CI, CH4) m/z 340 (M+1,98), 342 (33), 322 (100), 368 (M+29,22), 114 (26)

Workup

  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

Sources & evidence

ORD record
ord-62ab409b068649a887019e59e3f7cbb9
Source dataset
uspto-grants-1997_10
Patent number
US05681840

Reaction notes

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