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Furfural → (R/S)-3-(2-Furylmethyl)amino 1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

HRID 1436023
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HRID 1436023 반응식
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[C:12]3[C:13]([Br:21])=[CH:14][N:15]=[CH:16][C:17]=3[CH:18]=[CH:19][CH:20]=2)(=[O:10])=[O:9])[CH2:4]1.[CH:22](=O)[C:23]1[O:27][CH:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.C(N(CC)CC)C>[O:27]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:22][NH:2][CH:3]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[C:12]3[C:13]([Br:21])=[CH:14][N:15]=[CH:16][C:17]=3[CH:18]=[CH:19][CH:20]=2)(=[O:10])=[O:9])[CH2:4]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 7362FurfuralHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 672429033-Amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride

생성물 1

HCID 67244220(R/S)-3-(2-Furylmethyl)amino 1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine수율 27.3%

시약·촉매·용매 2

HCID 11
1,2-Dichloroethane
용매
HCID 8471Triethylamine용매

실험 절차

A suspension of 3-amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride (172 mg) obtained in Example 1 in 1,2-dichloroethane (10 ml) is added with triethylamine (0.28 ml, Wako Pure Chemical Industries), and then with furfural (42 mg, Aldrich), and the mixture is stirred at room temperature for 30 minutes, then added with sodium triacetoxyborohydride (170 mg, Aldrich), and further stirred at room temperature for 30 hours. The reaction mixture is added with saturated aqueous sodium hydrogencarbonate (15 ml), and the organic layer is separated. The aqueous layer is extracted 3 times with chloroform (10 ml for each time), and the combined organic layer is washed with saturated brine (30 ml). The organic layer is dried over anhydrous magnesium sulfate, and then the solvent is evaporated under reduced pressure. The residue is purified by silica gel chromatography (chloroform:methanol=30:1) to obtain the title compound (52 mg (predictive yield)).

후처리

  1. customthe organic layer is separated
  2. extractionThe aqueous layer is extracted 3 times with chloroform (10 ml for each time), and the combined organic layer
  3. washis washed with saturated brine (30 ml)
  4. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is purified by silica gel chromatography (chloroform:methanol=30:1)

출처 및 근거

ORD 기록
ord-f133c00155d644fb994730953c4ca1d9
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07618984B2

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