Tetrahydrofuran → 1-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

HRID 469322ノート

反応式

HRID 469322 の反応式
C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=2)[N:11]=1.[CH2:22]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C:30]1=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C[O:39]CC1>>[CH2:22]([N:29]1[CH2:34][CH2:33][C:32]([C:19]2[C:10]([Cl:9])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:20][CH3:21])=[CH:14][CH:13]=3)([OH:39])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 836472-Chloro-6-methoxyquinolineHCID 2724682Lithium diisopropylamideHCID 51700761-Benzyl-2-piperidone

生成物 1

HCID 581811261-Benzyl-4-(2-chloro-6-methoxyquinolin-3-yl)piperidin-4-ol

反応条件

温度
-78 °C

実験手順

Under an argon atmosphere 14.0 mL (28.0 mmol) of a 2 M lithium diisopropylamide solution in 50 mL THF were cooled to −78° C. and combined with stirring with a solution of 5.00 g (25.1 mmol) of 2-chloro-6-methoxy-quinoline in THF. After 1 h stirring at −78° C., 4.5 mL (25.2 mmol) N-benzylpiperidone were added dropwise. After 1 h stirring at −78° C. the mixture was allowed to come up to RT and stirred overnight. The mixture was evaporated down i. vac. and purified by flash chromatography through Alox. The fractions containing the product were combined and evaporated down.

後処理

  1. stirringAfter 1 h stirring at −78° C. the mixture
  2. customto come up to RT
  3. stirringstirred overnight
  4. customThe mixture was evaporated down i
  5. customand purified by flash chromatography through Alox
  6. additionThe fractions containing the product
  7. customevaporated down

出典と根拠

ORDレコード
ord-86951bac4dce423987c5afaee4886243
出典データセット
uspto-grants-2014_01
特許番号
US08629137B2

反応ノート

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