(r/s)-3 (Tert-butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine → (r/s)-3-(Tert-butoxycarbonylamino)-1-(4-ethyl-5-isoquinolinesulfonyl)pyrrolidine

HRID 1436035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436035
[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:27]=[CH2:28])=[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(O)C.[Pd]>[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]([CH2:27][CH3:28])=[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]

Komponenten

4

Edukt 1

HCID 67243428(r/s)-3 (Tert-butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine

Produkt 1

HCID 67243054(r/s)-3-(Tert-butoxycarbonylamino)-1-(4-ethyl-5-isoquinolinesulfonyl)pyrrolidineAusbeute 161,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of Intermediate 6 (120 mg) obtained in Example 9, Step A in ethanol (2 ml) is added with 10% palladium/activated carbon (90 mg, Wako Pure Chemical Industries), and the mixture is stirred at room temperature for 72 hours under a hydrogen gas atmosphere. The atmosphere is replaced with nitrogen gas, and then the insoluble matters are removed by filtration through Celite. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (195 mg (predictive yield)).

Aufarbeitung

  1. customthe insoluble matters are removed by filtration through Celite
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is purified by silica gel chromatography (n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-22032a70912b48e7bbca183482fe9485
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618984B2

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