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

HRID 1714803
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HRID 1714803 반응식
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
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참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cfdff44400e143589896ad34ce78093e
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07799775B2

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