Aluminium lithium hydride → HCID 68556385, compound

HRID 1804845Notes

Reaction equation

HRID 1804845 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH3:18])([C:14](OC)=[O:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:19][CH3:20].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][C:11]([CH2:14][OH:15])([CH3:18])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68556175HCID 68556175, compound

Product 1

HCID 68556385HCID 68556385, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 1-(4-chloro-3-methoxyphenyl)-4-methylpiperidine-4-carboxylate (500 mg, 1.679 mmol) in anhydrous THF (5 mL) and Et2O (10 mL) was treated dropwise with lithium aluminum hydride (3.36 mL of a 1.0 M solution in THF, 3.36 mmol) while the reaction temperature was controlled with a water bath. The mixture was then stirred at RT for 1 h, treated with Na2SO4.10H2O (1 g), stirred vigorously for 30 min and then dried with anhydrous MgSO4. The mixture was filtered and concentrated to give (1-(4-chloro-3-methoxyphenyl)-4-methylpiperidin-4-yl)methanol as a pale yellow oil (460 mg). The product was used without further purification in the subsequent step.

Workup

  1. customwas controlled with a water bath
  2. stirringstirred vigorously for 30 min
  3. dry with materialdried with anhydrous MgSO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fd303cc7fdc5490da3f9d97dffd9a2d4
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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