Triethylamine → {(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethyl}-methyl-amine

HRID 1633583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633583
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]([O:27][CH3:28])=[C:7]([C:9]2[CH2:10][CH2:11][N:12]([C:15](=O)[C@H:16]([NH:24][CH3:25])[CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH:14]=2)[CH:8]=1.C(N(CC)CC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:17]([C@@H:16]([NH:24][CH3:25])[CH2:15][N:12]1[CH2:13][CH2:14][C:9]([C:7]2[CH:8]=[C:3]([F:2])[CH:4]=[CH:5][C:6]=2[O:27][CH3:28])=[CH:10][CH2:11]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 21226445Aluminium lithium hydrideHCID 69692845HCID 69692845, Verbindung

Produkt 1

HCID 15512827{(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethyl}-methyl-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of (2R)-1-[4-(5-fluoro-2-methoxy-phenyl)-1,2,3,6-tetrahydropyridin-1-yl]-2-methylamino-3-phenyl-propan-1-one hydrochloride (0.41 g, 1.0 mmole) in 20 mL of tetrahydrofuran at 0° C. under N2 was added of triethylamine (0.14 mL, 1.0 mmol), followed by slow addition of 1.9 mL (1.9 mmole) lithium aluminum hydride (1 M solution in THF). After addition, the cooling bath was removed and the mixture was stirred at room temperature for 2.5 hours. The reaction was quenched by the slow addition of saturated NH4Cl solution and the mixture was filtered through a celite pad. The solution was concentrated to afford 0.36 g (100% {(1R)-1-benzyl-2-[4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridin-1-yl]-ethyl}-methyl-amine as a yellow oil which was used without further purification.

Aufarbeitung

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. customThe reaction was quenched by the slow addition of saturated NH4Cl solution
  4. filtrationthe mixture was filtered through a celite pad
  5. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-cf22e7ae1c254f85829b5576c0e5fbde
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503928B2

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