Aluminium lithium hydride → HCID 54358133, compound

HRID 1858104Notes

Reaction equation

HRID 1858104 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:33])=[C:24]([C:27](=[O:32])N(OC)C)[CH:25]=2)[NH:20][C:19](=[O:34])[C:18]=1[C:35]1[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([CH3:42])[CH:36]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:33])=[C:24]([CH:27]=[O:32])[CH:25]=2)[NH:20][C:19](=[O:34])[C:18]=1[C:35]1[CH:36]=[C:37]([CH3:42])[CH:38]=[C:39]([CH3:41])[CH:40]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53645995HCID 53645995, compound

Product 1

HCID 54358133HCID 54358133, compoundYield 84.6%

Procedure

To a solution of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-(methoxy-methylcarbamoyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (1.18 g in dry tetrahydrofuran) was added 3.9 mL of a 1M solution of lithium aluminum hydride and the mixture stirred at room temperature. After 2 hours, the reaction was quenched by the addition of saturated ammonium chloride solution. The mixture was filtered through diatomaceous earth and the filtrate extracted with ethyl acetate. The organics were then dried over magnesium sulfate and concentrated in vacuo to give the crude title compound (900 mg).

Workup

  1. customthe reaction was quenched by the addition of saturated ammonium chloride solution
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. extractionthe filtrate extracted with ethyl acetate
  4. dry with materialThe organics were then dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b9dcf7ada104f0b890fecf0f1d40f14
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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