(S)-3-(tert-Butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine → (S)-3-(tert-Butoxycarbonylamino)-1-(4-ethyl-5-isoquinolinesulfonyl)pyrrolidine

HRID 2425396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2425396
[C:1]([O:5][C:6]([NH:8][C@H: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][C@H: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 67244957(S)-3-(tert-Butoxycarbonylamino)-1-(4-vinyl-5-isoquinolinesulfonyl)pyrrolidine

Produkt 1

HCID 67243053(S)-3-(tert-Butoxycarbonylamino)-1-(4-ethyl-5-isoquinolinesulfonyl)pyrrolidineAusbeute 161,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a5578fdc38d1423687ed72ef4a137982
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964613B2

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