Triethylamine → 1,1-Dimethylethyl 7-({2-(methyloxy)-4-[(methyloxy)carbonyl]phenyl}oxy)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 222748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222748
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17](B(O)O)=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].[C:22]([O:33][CH3:34])(=[O:32])[C:23]1[CH:31]=[CH:30][C:28]([OH:29])=[C:25]([O:26][CH3:27])[CH:24]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:27][O:26][C:25]1[CH:24]=[C:23]([C:22]([O:33][CH3:34])=[O:32])[CH:31]=[CH:30][C:28]=1[O:29][C:17]1[CH:16]=[CH:15][C:12]2[CH2:13][CH2:14][N:8]([C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])[CH2:9][CH2:10][C:11]=2[CH:18]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 19844Methyl VanillateHCID 57440296(3-(tert-Butoxycarbonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)boronic acid

Produkt 1

HCID 574402971,1-Dimethylethyl 7-({2-(methyloxy)-4-[(methyloxy)carbonyl]phenyl}oxy)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(3-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)boronic acid (E264, Step 2) (500 mg, 1.72 mmol) was dissolved in dry dichloromethane (15 ml) and treated sequentially with methyl vanillate (313 mg, 1.72 mmol), molecular sieves (4 A, 1.0 g), copper acetate (467 mg, 2.58 mmol) and triethylamine (1.20 ml, 8.60 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane, filtered through celite and evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic portion was dried under magnesium sulfate and evaporated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of (0.1:9.9) to afford the title compound (240 mg). MS (ES+) m/e 328 [(M+H)—CO2tBu]+.

Aufarbeitung

  1. filtrationfiltered through celite
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. customThe organic portion was dried under magnesium sulfate
  6. customevaporated in vacuo
  7. customThe resulting residue was purified by column chromatography
  8. washeluting with a mixture of (0.1:9.9)

Quellen und Nachweise

ORD-Eintrag
ord-82d970880eea47b7a71431b262930f8e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207331B2

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