Triethylamine → (1R,5S)-3-methyl-8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane

HRID 449703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449703
Cl.Cl.[CH3:3][N:4]1[CH2:10][C@H:9]2[NH:11][C@H:6]([CH2:7][CH2:8]2)[CH2:5]1.F[C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[N:17][CH:18]=1.C(N(CC)CC)C>CS(C)=O.CCOC(C)=O>[CH3:3][N:4]1[CH2:10][C@H:9]2[N:11]([C:13]3[CH:18]=[N:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[C@H:6]([CH2:7][CH2:8]2)[CH2:5]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 167481095-Fluoro-2-nitropyridineHCID 66743274(1R,5S)-3-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride

Produkt 1

HCID 66742801(1R,5S)-3-methyl-8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octaneAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (1R,5S)-3-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (981 mg, 4.93 mmol), 5-fluoro-2-nitropyridine (100 mg, 4.93 mmol), and triethylamine (4.99 g, 49.3 mmol) in DMSO (8 ml) was heated to 80° C. for 2 hr. After cooling to room temperature, the reaction mixture was diluted with EtOAc and washed with saturated ammonium chloride, and water. The organic phase was then concentrated and triturated with ether to give desire product as an yellow solid (1 g, 81.8%).

Aufarbeitung

  1. washwashed with saturated ammonium chloride, and water
  2. concentrationThe organic phase was then concentrated
  3. customtriturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-f92acff430b64b739ac0ef8dcf092b11
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481540B2

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