2,2,6,6-Tetramethylpiperidine → (2'R,6'S)-1'-[2-(2-benzyl-1 H-pyrazol-4-yl)-ethyl]-3,3''-dimethyl-1',2',3',4',5',6'-hexahydro-[2,2';6',2'']terpyridine

HRID 1987325ノート

反応式

HRID 1987325 の反応式
[CH3:1][C:2]1[C:3]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:21]([N:28]1[CH2:32][C:31]([CH2:33][CH2:34]OS(C)(=O)=O)=[CH:30][NH:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC1(C)CCCC(C)(C)N1>CC#N>[CH2:21]([N:28]1[CH2:32][C:31]([CH2:33][CH2:34][N:9]2[C@H:8]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[CH2:13][CH2:12][CH2:11][C@@H:10]2[C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:30][NH:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 575911373,3''-Dimethyl-1',2',3',4',5', 6'-hexahydro-cis-[2,2';6',2'']terpyridineHCID 86597121methanesulfonic acid 2-(2-benzyl-1H-pyrazol-4-yl)-ethyl ester

生成物 1

HCID 86597120(2'R,6'S)-1'-[2-(2-benzyl-1 H-pyrazol-4-yl)-ethyl]-3,3''-dimethyl-1',2',3',4',5',6'-hexahydro-[2,2';6',2'']terpyridine収率 93%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of (2′R,6′S)-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′2″]terpyridine (0.320 g, 1.20 mmol), methanesulfonic acid 2-(2-benzyl-1 H-pyrazol-4-yl)-ethyl ester (0.540 g, 1.60 mmol) and 2,2,6,6-tetramethylpiperidine (0.255 g, 1.80 mmol) in CH3CN (5 mL) was stirred and heated at reflux overnight. The solvent was then removed, water (20 mL) was added, and the mixture was extracted with CH2Cl2 (3×20 mL). The extracts were combined and dried over Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (500:15:1 CH2Cl2/CH3OH/NH4OH), affording (2′R,6′S)-1′-[2-(2-benzyl-1H-pyrazol-4-yl)-ethyl]-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine as a pale yellow oil (0.420 g, 93%).

後処理

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was then removed
  4. additionwater (20 mL) was added
  5. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration the solvent
  8. customwas removed by evaporation under vacuum
  9. customthe residue was purified by flash chromatography on a silica gel column (500:15:1 CH2Cl2/CH3OH/NH4OH)

出典と根拠

ORDレコード
ord-494041b838574bb1bb31449b83da0613
出典データセット
uspto-grants-2009_06
特許番号
US07550484B2

反応ノート

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