2,6-Di-tert-butyl-4-methylphenol → (r/s)-3 (Tert-butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine

HRID 1436027노트

반응식

HRID 1436027 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19](Br)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28](C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)[CH3:29].C(C([Sn])=C(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([CH:28]=[CH2:29])=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 53438229Tri(butyl)vinyltinHCID 67242856(r/s)-3-(Tert-butoxycarbonylamino)-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

생성물 1

HCID 67243428(r/s)-3 (Tert-butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine수율 21,298.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A solution of Intermediate 1 (250 mg) obtained in Example 1, Step A, 2,6-di(tert-butyl)-4-methylphenol (0.5 mg, Tokyo Kasei Kogyo), and tri(n-butyl)vinyltin (0.25 ml, Tokyo Kasei Kogyo) in toluene (8 ml) is added with tetrakis(triphenylphosphine)palladium(0) (13 mg, Kanto Chemicals) under a nitrogen gas atmosphere, and the mixture is refluxed by heating for 12 hours. The reaction mixture is cooled to room temperature, and then the solvent is evaporated under reduced pressure. The residue is purified by silica gel chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (195 mg (predictive yield)).

후처리

  1. temperaturethe mixture is refluxed
  2. temperatureby heating for 12 hours
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel chromatography (n-hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-38188c521415438e8ebb1fe623cbea97
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618984B2

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