HCID 18475834, compound → HCID 18475823, compound

HRID 2187887Notes

Reaction equation

HRID 2187887 reaction equation
C(O[C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:25][O:24][CH2:23][CH2:22][O:21][CH2:20][O:19][C:16]1[CH:17]=[C:18]2[C:13]([CH:12]=[CH:11][CH:10]=[C:9]2[NH:8][CH3:6])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 18475834HCID 18475834, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18475823HCID 18475823, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(tert-butoxycarbonylamino)-7-[(2-methoxyethoxy)methoxy]naphthalene, as described above in Step A, (1.59 g, 4.58 mmol) and LAH (11.4 mL of a 1.0 M solution in THF, 11.4 mmol) in dry THF (100 mL) was heated to 65° C., under argon. After 70 min, the reaction mixture was cooled to ambient temperature and quenched with saturated aqueous NH4Cl (5 mL). Most of the THF was removed by concentration under reduced pressure, and the residual mixture was partitioned between water (500 mL) and CH2Cl2 (250 mL). The aqueous layer was extracted further with CH2Cl2 (250 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane −25% EtOAc to yield the titled product.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. customquenched with saturated aqueous NH4Cl (5 mL)
  3. customMost of the THF was removed by concentration under reduced pressure
  4. customthe residual mixture was partitioned between water (500 mL) and CH2Cl2 (250 mL)
  5. extractionThe aqueous layer was extracted further with CH2Cl2 (250 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash column chromatography on silica
  10. washeluting with hexane −25% EtOAc

Sources & evidence

ORD record
ord-cdf1237c210642cfbffe12afaaf536be
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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