1,4-Dioxane → (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-formylisoquinolin-3-yl)ethylcarbamate

HRID 1626935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626935
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=C)=[N:9][C:8]([C@@H:14]([NH:16][C:17](=[O:33])[O:18][CH2:19][CH:20]1[C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:26]3[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH3:15])=[CH:7]2.[O:34]1CCOCC1>O.O=[Os](=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=[O:34])=[N:9][C:8]([C@@H:14]([NH:16][C:17](=[O:33])[O:18][CH2:19][CH:20]1[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[C:27]3[C:32]1=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:15])=[CH:7]2

Komponenten

5

Edukt 2

HCID 312751,4-DioxaneHCID 69097659HCID 69097659, Verbindung

Produkt 1

HCID 86677063(S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-formylisoquinolin-3-yl)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a suspension of (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-vinylisoquinolin-3-yl)ethylcarbamate (347) (10.6 g, 23.3 mmol, 1.0 eq) in 1,4-dioxane (200 mL) and water (100 mL), OsO4 (50 mg) was added and the resulting mixture was stirred at RT for 30 min. To this mixture, NaIO4 (15 g, 69.9 mmol, 3.0 eq) was added, and then the mixture was stirred at RT for 16 h. The mixture reaction was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (5-20% ethyl acetate-petro ether) to afford (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-l-formylisoquinolin-3-yl)ethylcarbamate (348).

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred at RT for 16 h
  3. customThe mixture reaction
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe organic layer was washed with water (2×100 mL) and brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel (5-20% ethyl acetate-petro ether)

Quellen und Nachweise

ORD-Eintrag
ord-12592a70549e4b089ef88d3e430d211d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785470B2

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