Carbon Dioxide → N-[(S)-6-(1-hydroxy-1-methylethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913823
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:27])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:16][CH:15]=1)[CH2:6][CH2:5]2.C(=O)=[O:29].C[Li].[CH2:33]([Li])[CH2:34][CH2:35]C>O.CC(C)=O.C1COCC1>[OH:29][C:34]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@@H:7]([NH:12][C:13](=[O:27])[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][C@@H:22]3[CH2:26][CH2:25][CH2:24][O:23]3)=[CH:18][CH:19]=1)[CH2:6][CH2:5]2)([CH3:35])[CH3:33]

Komponenten

8

Edukt 4

HCID 280Carbon DioxideHCID 67545579N-((S)-6-Bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamideHCID 178418339ButyllithiumHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 67545052N-[(S)-6-(1-hydroxy-1-methylethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of N-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (1.0 g) and THF (10 ml) was cooled to −78° C. (dry ice bath), and a solution of methyllithium (2.0 ml; 1.6 M in diethyl ether) was added dropwise. One minute after the addition had ended, a solution of butyllithium (1.4 ml; 2.5 M in toluene) was added dropwise. One minute after the addition had ended, acetone (0.14 g) was added. After warming to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phases were dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel (eluent: 1:2 heptane/ethyl acetate). The product was thus obtained with the molecular weight of 409.53 (C25H31NO4); MS (ESI): 410 (M+H+).

Aufarbeitung

  1. additionOne minute after the addition
  2. additionOne minute after the addition
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phases were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (eluent: 1:2 heptane/ethyl acetate)
  7. customThe product was thus obtained with the molecular weight of 409.53 (C25H31NO4)

Quellen und Nachweise

ORD-Eintrag
ord-d6722344340a4c2ab51968ac4126f02f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609731B2

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