Ethyl bromoacetate → 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene

HRID 380109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380109
ClCCl.B(Br)(Br)Br.[CH3:8][N:9]([CH:28]1[C:36]2[C:31](=[C:32]([OH:37])[CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1)[CH2:10][C:11]1[O:12][C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1.Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].C([O-])([O-])=O.[K+].[K+]>ClCCl.CN(C=O)C>[CH3:8][N:9]([CH:28]1[C:36]2[C:31](=[C:32]([O:37][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1)[CH2:10][C:11]1[O:12][C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:15]=1

Komponenten

7

Edukt 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 183672371-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indeneHCID 22277759Boron tribromide dichloromethane

Produkt 1

HCID 183673111-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indeneAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1-[N-methyl-N-[(4,5-diphenyloxazol-2.-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (109 mg) in dichloromethane (2 ml) was added 1M boron tribromide dichloromethane solution (1 ml) at 0° C. After being stirred for 4 hours at 0° C., the solvent was evaporated in vacuo. The residue was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated in vacuo to afford crude 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg). To a solution of crude 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg) and ethyl bromoacetate (80 mg) in DMF (3 ml) was added K2CO3 (80 mg). After being stirred for 24 hours, the solution was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene (80 mg).

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe mixture was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customto afford crude 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg)
  7. stirringAfter being stirred for 24 hours
  8. extractionthe solution was extracted with ethyl acetate
  9. washThe mixture was washed with brine
  10. dry with materialdried over MgSO4
  11. customevaporated in vacuo
  12. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7c73874897b84d00a0f8b693aa129af1
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300344B1

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