Tetrahydrofuran → HCID 21939867, compound

HRID 1242926Notes

Reaction equation

HRID 1242926 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]([NH:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([CH2:26][C:27](OC)=[O:28])[CH2:20][CH2:19]2)(=[O:14])[CH3:13]>C(OCC)(=O)C>[OH:28][CH2:27][CH2:26][C:21]1[CH2:20][CH2:19][C:18]2[CH:17]=[C:16]([NH:15][C:12](=[O:14])[CH3:13])[CH:25]=[CH:24][C:23]=2[CH:22]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21063014HCID 21063014, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21939867HCID 21939867, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Lithium aluminum hydride (242 mg, 6.38 mmol) was added to a tetrahydrofuran solution (16 ml) of methyl [6-(acetylamino)-3,4-dihydro-2-naphthalenyl]acetate (827 mg, 3.19 mmol) obtained in Reference Example 101 under ice-cooling, which was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, which was washed with 1N hydrochloric acid and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The residue was powdered with isopropyl ether, to give the titled compound (364 mg).

Workup

  1. customobtained in Reference Example 101 under ice-
  2. temperaturecooling
  3. washwas washed with 1N hydrochloric acid and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-d53c32872e7441b5be509f1f680d5ddc
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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