Methanol → HCID 21063014, compound

HRID 1242925Notes

Reaction equation

HRID 1242925 reaction equation
[BH4-].[Na+].CO.[C:5]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=O)[CH:14]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:13][CH2:12]2)(=[O:7])[CH3:6].S(=O)(=O)(O)O>C(O)(=O)C.C(OCC)(=O)C>[C:5]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:13][CH2:12]2)(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 21063015HCID 21063015, compound

Product 1

HCID 21063014HCID 21063014, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (72.4 mg, 1.91 mmol) was added to a methanol solution (10 ml) of methyl [6-(acetylamino)-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl]acetate (527 mg, 1.91 mmol) obtained in Reference Example 100 under ice-cooling, which was stirred for 1 hour. Ethyl acetate was added to the reaction mixture, which was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by alumina B column chromatography (development solvent; ethyl acetate). Concentrated sulfuric acid (0.14 ml) was added to an acetic acid solution (7 ml) of the oil (404 mg, 1.46 mmol), which was stirred at 40° C. for 5 hours. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1), to give the titled compound (251 mg).

Workup

  1. customobtained in Reference Example 100 under ice-
  2. temperaturecooling
  3. washwas washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resulting oily substance was purified by alumina B column chromatography (development solvent; ethyl acetate)
  7. stirringwas stirred at 40° C. for 5 hours
  8. distillationThe solvent was distilled out under reduced pressure
  9. additionEthyl acetate was added to the residue, which
  10. washwas washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled out under reduced pressure
  13. customThe resulting oily substance was purified by silica gel column chromatography (development solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-83f91ea771694821aa87b51a73f86362
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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