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Diazomethane → (3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine

HRID 1010562
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HRID 1010562 반응식
[N+](=[CH2:3])=[N-].[CH2:4]([O:11][C:12]([N:14]1[CH2:18][C@H:17]([CH:19]=[CH2:20])[C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:4]([O:11][C:12]([N:14]1[CH2:18][C@H:17]([CH:19]2[CH2:3][CH2:20]2)[C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:15]1)=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
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참가 물질

5

반응물 2

HCID 9550DiazomethaneHCID 59665269(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine

생성물 1

HCID 53837949(3S,4S)-1-Benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-cyclopropylpyrrolidine

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매

실험 절차

An excessive amount of a solution of diazomethane in diethyl ether (30 mL) was added to (3S,4S)-1-benzyloxycarbonyl-3-(tert-butoxycarbonyl)amino-4-vinylpyrrolidine (270 mg, 779 mmol). Under cooling with ice, palladium acetate (10 mg) was added thereto, followed by stirring at room temperature for 2 hours. After completion of reaction, insoluble matter was removed through filtration. The filtrate was concentrated under reduced pressure, and the obtained residue was purified though silica gel column chromatography (ethyl acetate:n-hexane=1:9 to 1:4), to thereby yield the title compound as a colorless oily substance (269 mg, 96%).

후처리

  1. additionwas added
  2. customAfter completion of reaction, insoluble matter
  3. customwas removed through filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified though silica gel column chromatography (ethyl acetate:n-hexane=1:9 to 1:4)

출처 및 근거

ORD 기록
ord-adb8be1ebc5e4f6db1dfa290b564b6d8
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977327B2

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