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

HRID 2425378
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2425378
Cl.[NH2:2][C@H: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][C@H: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
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Komponenten

7

Edukt 4

HCID 7362FurfuralHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67244372(S)-3-amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine hydrochloride

Produkt 1

HCID 16223986(S)-3-(2-Furylmethyl)amino-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidineAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 111,2-DichloroethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e6f6201477724845a036b9dd614b3873
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07964613B2

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