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Water → 2-((S)-1-(8-chloro-2-(1,2-dihydroxyethyl)quinolin-3-yl)ethyl)isoindoline-1,3-dione

HRID 2044894
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2044894
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[CH2:13])[C:8]([C@@H:14]([N:16]1[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]1=[O:26])[CH3:15])=[CH:7]2.C[N+]1([O-])CC[O:31]CC1.[OH2:35]>C1COCC1.C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O.O.[O-][Os]([O-])(=O)=O.[K+].[K+]>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]([OH:31])[CH2:13][OH:35])[C:8]([C@@H:14]([N:16]1[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]1=[O:26])[CH3:15])=[CH:7]2
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Komponenten

8

Edukt 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 57707765(S)-2-(1-(8-chloro-2-vinylquinolin-3-yl)ethyl)isoindoline-1,3-dione

Produkt 1

HCID 577079722-((S)-1-(8-chloro-2-(1,2-dihydroxyethyl)quinolin-3-yl)ethyl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 53393272Potassium osmate(VI) dihydrate
Katalysator
HCID 311Citric AcidLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-2-(1-(8-chloro-2-vinylquinolin-3-yl)ethyl)isoindoline-1,3-dione (200 mg, 0.55 mmol) in THF (5 mL) and water (1.0 mL) was added potassium osmate(VI) dihydrate (10.2 mg, 27.6 μmol). The reaction was stirred for 5 minutes and then NMO (64.6 mg, 0.55 mmol) was added. The reaction was stirred for 3 hours and then it was diluted with ethyl acetate (80 mL) and 1.0 M aqueous citric acid (40 mL). The separated aqueous layer was extracted with ethyl acetate (140 mL) and the combined organic layers were washed with brine (40 mL), dried (MgSO4), filtered and evaporated in vacuo to give 2-((S)-1-(8-chloro-2-(1,2-dihydroxyethyl)quinolin-3-yl)ethyl)isoindoline-1,3-dione. The product was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ ppm 8.77 (1H, d, J=11.7 Hz), 7.61-7.88 (6H, m), 7.49 (1H, q, J=8.1 Hz), 5.95-6.17 (1H, m), 5.22-5.32 (1H, m), 4.02-4.26 (2H, m), 1.94-1.97 (3H, m). Mass Spectrum (ESI) m/e=396.9 (M+1).

Aufarbeitung

  1. stirringThe reaction was stirred for 3 hours
  2. extractionThe separated aqueous layer was extracted with ethyl acetate (140 mL)
  3. washthe combined organic layers were washed with brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0b474d206565452c951a1d9893f88dad
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08586739B2

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