Ethyl chloroformate → Ethyl [5-methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenyl]carbamate

HRID 1433956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433956
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)=[C:7]([NH2:9])[CH:8]=1.[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25].[Cl-].[NH4+]>O1CCCC1.C(N(CC)C(C)C)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)=[C:7]([NH:9][C:22](=[O:26])[O:23][CH2:24][CH3:25])[CH:8]=1

Komponenten

6

Edukt 3

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 230872185-Methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenylamine

Produkt 1

HCID 86605239Ethyl [5-methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

To a solution of 5-methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenylamine (400 mg) in tetrahydrofuran (10 ml) and N,N-diisopropylethylamine (0.5 ml) was added ethyl chlorocarbonate (0.2 ml) on an ice bath, and the solution was stirred overnight at room temperature. A saturated aqueous solution of ammonium chloride was added thereto, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide ethyl [5-methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenyl]carbamate (445 mg). This compound (438 mg) was used according to an analogous synthetic method to Example 337 described below to provide the title compound (286 mg).

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate
  2. washsequentially washed with water and brine
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-f26cdc604ad34543bdf42326fb58a932
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612114B2

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