Water → HCID 22449061, compound

HRID 2186735Notes

Reaction equation

HRID 2186735 reaction equation
C([O:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14](=O)[N:15]([CH2:16][C:17](OC)=[O:18])[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[OH:18][CH2:17][CH2:16][N:15]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:4])[C:10]=2[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54220897HCID 54220897, compound

Product 1

HCID 22449061HCID 22449061, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl (6-acetoxy-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetate (1080 mg) was dissolved in THF (15 ml) under an argon atmosphere, and the resultant solution was stirred at 0° C. Lithium aluminum hydride (355 mg) was added to the solution, and the mixture was stirred at 0° C. After disappearance of the raw materials was confirmed, the reaction solution was added to water (100 ml), and then extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated. The resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=2/1) to obtain the object compound (624 mg, yield 81%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4652808059764f47a5f0b1d695df8f15
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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