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

HRID 1721804Notes

Reaction equation

HRID 1721804 reaction equation
[CH:1]1[C:14]2[C:13]3([C:16]([N:18]4[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]4)=O)[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH:11]1[C:12]2[C:13]3([CH2:16][N:18]4[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]4)[CH2:15][CH:6]([C:5]4[C:14]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21480612HCID 21480612, compound

Product 1

HCID 214806171-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)piperidin-4-olYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled suspension (0° C.) of-(9,10-dihydro-9,10-methanoanthracen-9-ylcarbonyl)piperidin-4-ol (described above)(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 the title compound as a white solid in 88% yield. TLC analysis (Rf 0.54, 10% methanol in CHCl3) MS (Cl, CH4) m/z 306 (M+1,100), 334 (M+29,14), 288 (62), 114 (8).

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-b033dc5036744c4994fd089826acfe0a
Source dataset
uspto-grants-1996_04
Patent number
US05512575

Reaction notes

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