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Diisopropylamine → 2-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonyl-3-oxopiperazine

HRID 1714803
ノート
印刷プレビュー

反応式

HRID 1714803 の反応式
CCCCCC.C([Li])CCC.C(NC(C)C)(C)C.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][C:28](=[O:32])[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].Cl[CH2:34][C:35]1[CH:43]=[CH:42][C:38]2[O:39][CH2:40][O:41][C:37]=2[CH:36]=1.[Cl-].[NH4+]>O1CCCC1>[O:39]1[C:38]2[CH:42]=[CH:43][C:35]([CH2:34][CH:27]3[C:28](=[O:32])[NH:29][CH2:30][CH2:31][N:26]3[C:24]([O:23][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:25])=[CH:36][C:37]=2[O:41][CH2:40]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 178418244HCID 178418244、化合物

生成物 1

HCID 231559092-Benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonyl-3-oxopiperazine収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Under argon atmosphere, 17.5 ml of 1.58M n-butyl lithium-n-hexane solution was dropped into a mixture of 25 ml of tetrahydrofuran and 2.78 g of diisopropylamine under cooling ice, followed by 30 minutes' stirring under the same condition. Thereafter a solution of 2.50 g of 1-tert-butoxycarbonyl-3-oxopiperazine (which was prepared by following Tetrahedron Lett., 1980, 21, 3019-3020) in 60 ml of tetrahydrofuran was added by dropping under cooling with ice, followed by 3 hours' stirring under the same condition, further dropping of a solution of 2.30 g of 5-chloromethyl-benzo[1,3]dioxole in 20 ml of tetrahydrofuran under cooling with ice, and an hour's stirring under the same condition. The solution was warmed to room temperature and stirred for 18 hours. After addition of saturated aqueous ammonium chloride solution, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and the solvent was distilled therefrom under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate) to provide 2.84 g (68%) of 2-benzo[1,3]dioxol-5-ylmethyl-1-tert-butoxycarbonyl-3-oxopiperazine.

後処理

  1. temperatureunder cooling with ice
  2. waitfollowed by 3 hours
  3. temperatureunder cooling with ice, and an hour's
  4. stirringstirring under the same condition
  5. stirringstirred for 18 hours
  6. extractionthe solution was extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled
  9. customThe residue was purified on silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-cfdff44400e143589896ad34ce78093e
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07799775B2

反応ノート

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