4-Methylmorpholine → HCID 59483857, Verbindung

HRID 1808381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808381
Cl.Cl.[N:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:27]([O:31][C:32]([N:34]1[CH2:43][CH2:42][C:41]2[C:36](=[C:37]([C:44](O)=[O:45])[CH:38]=[CH:39][CH:40]=2)[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[N:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][N:17]([C:44]([C:37]4[CH:38]=[CH:39][CH:40]=[C:41]5[C:36]=4[CH2:35][N:34]([C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])[CH2:43][CH2:42]5)=[O:45])[CH2:16][CH2:15]3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 450740022-[(Tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acidHCID 66701057HCID 66701057, Verbindung

Produkt 1

HCID 59483857HCID 59483857, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(Pyridin-4-yl)-3,9-diazaspiro[5.5]undecane dihydrochloride (F-09) (0.49 g, 1.62 mmol) was dissolved in DMF and triethylamine (0.45 g, 3.25 mmol), and 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid (0.45 g, 1.62 mmol) (available commercially from Ennova, for example) was added, followed by benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.93 g, 2.11 mmol) and 4-methylmorpholine (0.53 g, 4.87 mmol). The reaction mixture was stirred for 15 h at RT, and then the solvent was removed in vacuo. The residue was taken up in ethyl acetate and sat. sodium hydrogen carbonate solution, and the phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with sat. sodium hydrogen carbonate solution and sat. sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol 20:1+ammonia solution (25% aq.)). Yield: 0.78 g (98%).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customsat. sodium hydrogen carbonate solution, and the phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic phases were washed with sat. sodium hydrogen carbonate solution and sat. sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/methanol 20:1+ammonia solution (25% aq.))

Quellen und Nachweise

ORD-Eintrag
ord-85061c16c22f46f599f349a97a79b561
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357717B2

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