Water → HCID 23114214, compound

HRID 1787200Notes

Reaction equation

HRID 1787200 reaction equation
[NH2:1][C:2]1[C:3]([CH3:28])=[C:4]([CH2:21][CH2:22][C:23](OCC)=[O:24])[C:5]2[O:9][CH2:8][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=3)[C:6]=2[C:19]=1[CH3:20].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[NH2:1][C:2]1[C:3]([CH3:28])=[C:4]([CH2:21][CH2:22][CH2:23][OH:24])[C:5]2[O:9][CH2:8][CH:7]([C:10]3[CH:11]=[CH:12][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:15]=3)[C:6]=2[C:19]=1[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 23113888HCID 23113888, compound

Product 1

HCID 23114214HCID 23114214, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 3-(5-amino-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-7-yl)propanoate synthesized in Reference Example 321 (1.28 g, 3.36 mmol) in THF, was added Lithium aluminum hydride (255 mg, 6.72 mmol) at 0° C., and the mixture was stirred at the same temperature for 30 minutes and heated under reflux for 30 minutes. To the reaction solution was added water, and the product was extracted with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was crystallized from hexane-ethyl acetate to obtain 750 mg (yield 66%) of the title compound. Melting point: 110-111° C. (hexane-ethyl acetate).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe combined extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-5ef7918283814704bb2b50ea56370c86
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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