(5S,6S,9R)-5-azido-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine → 5H-Cyclohepta[b]pyridin-5-amine, 6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-9-[[tris(1-methylethyl)silyl]oxy]-, (5S,6S,9R)-

HRID 1879383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879383
[N:1]([C@@H:4]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]([O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH2:7][CH2:6][C@H:5]1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[F:33])=[N+]=[N-]>C(O)C.[Pd]>[F:33][C:27]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:26]=1[C@@H:5]1[CH2:6][CH2:7][C@@H:8]([O:15][Si:16]([CH:20]([CH3:22])[CH3:21])([CH:23]([CH3:25])[CH3:24])[CH:17]([CH3:18])[CH3:19])[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:14]2[C@H:4]1[NH2:1]

Komponenten

4

Edukt 1

HCID 71533837(5S,6S,9R)-5-azido-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine2×

Produkt 1

HCID 671158635H-Cyclohepta[b]pyridin-5-amine, 6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-9-[[tris(1-methylethyl)silyl]oxy]-, (5S,6S,9R)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (5S,6S,9R)-5-azido-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (598 mg, 1.265 mmol)(intermediate 9) and palladium (10% on activated carbon) (0.504 mg, 0.474 μmol) in ethanol (25 ml) was stirred under hydrogen (1 atm) for 2.5 h. LCMS indicated that the desired compound was formed, stirring was continued. After 5 h, the mixture was filtered, washed thoroughly with ethanol, and then concentrated to give 21 (525 mg, 93%) as a colorless oil: MS(ESI)[M+H+]=447.3.

Quellen und Nachweise

ORD-Eintrag
ord-f84263a287e748c9bb11fa77ea57ca16
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314117B2

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