Diisopropylamine → HCID 86649625、化合物

HRID 1897947ノート

反応式

HRID 1897947 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.[Br:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]Br)[N:33]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Br:31][C:32]1[N:33]=[C:34]([CH2:38][C:16]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14][N:13]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:18][CH2:17]2)[CH:35]=[CH:36][CH:37]=1

参加物

8

反応物 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 178418339Butyllithium

生成物 1

HCID 86649625HCID 86649625、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 0.855 ml of diisopropylamine in 15 ml of tetrahydrofuran was added 2.26 ml of a hexane solution containing 2.66 M n-butyllithium at 0° C., followed by stirring the reaction mixture at 0° C. for 30 minutes. After cooling down to −78° C., a solution of 1.54 g of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate in 5 ml of tetrahydrofuran was added to the reaction mixture, and the resultant mixture was stirred at −78° C. for 30 minutes. A solution of 1.00 g of 2-bromo-6-(bromomethyl)pyridine in 5 ml of tetrahydrofuran was added to the reaction mixture, followed by stirring the reaction mixture at −78° C. for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by extracting with ethyl acetate. The resulting ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−2/1) to give the title compound as a yellow oil.

後処理

  1. temperatureAfter cooling down to −78° C.
  2. stirringby stirring the reaction mixture at −78° C. for 2 hours
  3. extractionby extracting with ethyl acetate
  4. dry with materialThe resulting ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−2/1)

出典と根拠

ORDレコード
ord-e0d52fcf95b74e7883427860c2098790
出典データセット
uspto-grants-2013_08
特許番号
US08519136B2

反応ノート

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