(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 1879383ノート

反応式

HRID 1879383 の反応式
[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]

参加物

4

反応物 1

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

生成物 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)-

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-f84263a287e748c9bb11fa77ea57ca16
出典データセット
uspto-grants-2012_11
特許番号
US08314117B2

反応ノート

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