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Methanol → (R)-2-Methyl-1-oxo-1-(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-yl acetate

HRID 445279
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 445279
[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]([O:33][C:34]([C:37](Cl)=[O:38])([CH3:36])[CH3:35])(=[O:32])[CH3:31].CO>C(Cl)Cl>[C:30]([O:33][C:34]([CH3:36])([CH3:35])[C:37](=[O:38])[N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=1)(=[O:32])[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 1234962-Acetoxyisobutyroyl chloride2×HCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 59536313(R)-2-Methyl-1-oxo-1-(1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2(1H)-yl)propan-2-yl acetate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (207 mg, 747 μmol, example 30 (step 1) and DIEA (130 μL, 747 μmol) in DCM (2.5 mL) was added 1-chlorocarbonyl-1-methylethyl acetate (119 μL, 821 μmol). The mixture was stirred at RT for 3 h. Then, 1-chlorocarbonyl-1-methylethyl acetate (50 μL) was added and the mixture was stirred at RT for 16 h. MeOH (1 mL) was added and the mixture was filtered. The filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/water 0.1% TFA) to give the title compound in a solution of H2O 0.1% TFA and MeCN 0.1% TFA. The solvent was removed and saturated NaHCO3 (5 mL) was added. The mixture was extracted with EtOAc (2×30 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to give the title compound as a white solid. MS (ESI, positive ion) m/z: 406 (M+H).

Aufarbeitung

  1. stirringthe mixture was stirred at RT for 16 h
  2. filtrationthe mixture was filtered
  3. customThe filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/water 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-1788a70662394664921c8942a9e49528
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476297B2

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