Water → HCID 59536317, Verbindung

HRID 445280

Reaktionsgleichung

Reaktionsgleichung von HRID 445280
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:30](OC(=O)C)(=[O:32])[CH3:31].O>C(Cl)Cl>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:30](=[O:32])[CH3:31])=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 59536317HCID 59536317, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (100 mg, 361 μmol, example 30 (step 1) in DCM (2 mL) was added DIEA (62.8 μL, 361 μmol) and acetic acid anhydride (34.0 μL, 361 mop. The resulting mixture was then stirred at RT for 16 h. Then, H2O (1 mL) was added and the mixture was extracted with DCM (2×5 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel flash column chromatography (0%-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 320 (M+H).

Aufarbeitung

  1. extractionthe mixture was extracted with DCM (2×5 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash column chromatography (0%-100% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e667baa622fb4363bb0e5c38b9512651
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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