Aluminium lithium hydride → HCID 22645410, compound

HRID 2414274Notes

Reaction equation

HRID 2414274 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:24])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](OC)=[O:21])[CH:15]=2)[CH:10]([CH3:25])[CH2:9]1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:24])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][OH:21])[CH:15]=2)[CH:10]([CH3:25])[CH2:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22645401HCID 22645401, compound

Product 1

HCID 22645410HCID 22645410, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1-hexanoyl-3,4-dimethyl-4-(3-methoxycarbonyl-phenyl)piperidine (Preparation 7, 80 mg, 0.23 mmol) in anhydrous tetrahydrofuran (1 mL) under nitrogen was treated with lithium aluminium hydride (1.0 M in ether, 0.70 mL, 0.70 mmol) and the mixture was stirred at room temperature for 3 hours. The reaction mixture was then quenched with water (7.5 mL) and extracted with ethyl acetate (7 mL). The phases were separated and the aqueous layer was further extracted with ethyl acetate (2×5 mL). The combined organics were dried (Na2SO4) and the solvent removed in vacuo to give the title compound as a pale oil (30 mg).

Workup

  1. customThe reaction mixture was then quenched with water (7.5 mL)
  2. extractionextracted with ethyl acetate (7 mL)
  3. customThe phases were separated
  4. extractionthe aqueous layer was further extracted with ethyl acetate (2×5 mL)
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a22244b33c104468a5bedc474d0b89ec
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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