Tetrabutylammonium Fluoride Trihydrate → 5-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-one

HRID 1925503ノート

反応式

HRID 1925503 の反応式
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)=[C:39]5[C:34]=4[CH:35]=[CH:36][C:37](=[O:51])[NH:38]5)[O:25][Si](C(C)(C)C)(C)C)[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)=[C:39]5[C:34]=4[CH:35]=[CH:36][C:37](=[O:51])[NH:38]5)[OH:25])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

参加物

4

反応物 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 675208935-((1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-8-(benzyloxy)quinolin-2(1H)-one

生成物 1

HCID 675206375-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-one収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a solution of Intermediate 32 (0.48 g, 0.68 mmol) in tetrahydrofuran (12 mL) was added tetrabutylammonium fluoride trihydrate (0.284 g, 1.09 mmol). The reaction mixture was stirred at 45° C. for 3.5 hours. The solvent was removed under reduced pressure and the crude was partitioned between ethyl acetate and water. The organic layer was washed several times with water and the solvent was removed under reduced pressure to give the title compound as a yellow solid (0.375 g, 88%). MS (M+): 593.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe crude was partitioned between ethyl acetate and water
  3. washThe organic layer was washed several times with water
  4. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-a23753e32f414c7b91506d663dbea864
出典データセット
uspto-grants-2012_05
特許番号
US08178679B2

反応ノート

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