Sodium Sulfite → 3-[8-Chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-(hydroxymethyl)cyclobutanol

HRID 244193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244193
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:30][C:29](=[CH2:31])[CH2:28]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.C[N+]1([O-])CC[O:36]CC1.[O-]S([O-])=O.[Na+].[Na+].C1COCC1.[OH2:51]>CCOC(C)=O>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:30][C:29]([CH2:31][OH:36])([OH:51])[CH2:28]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1

Komponenten

6

Edukt 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 536290387-(8-Chloro-3-(3-methylenecyclobutyl)imidazo[1,5-a]pyrazin-1-yl)-2-phenylquinoline

Produkt 1

HCID 536290393-[8-Chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-(hydroxymethyl)cyclobutanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 7-[8-chloro-3-(3-methylenecyclobutyl)imidazo[1,5-a]pyrazin-1-yl]-2-phenylquinoline (3.2 g, 7.6 mmol) in THF-water mixture (100 mL, 3:1) were added NMO (1.94 g, 8.3 mmol) and potassium osmate dihydrate (0.14 g, 0.4 mmol). The reaction mixture was stirred at rt. After 20 h the reaction was quenched with Na2SO3 (4.8 g, 38 mmol). The reaction mixture was diluted with EtOAc (250 mL) and washed with brine (2×100 mL). Part of the solvent was removed and the organic phase was passed through celite, dried over anhydrous Na2SO4 and concentrated in vacuo. The material was carried on to the subsequent oxidation without further purification.

Aufarbeitung

  1. washwashed with brine (2×100 mL)
  2. customPart of the solvent was removed
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe material was carried on to the subsequent oxidation without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8c1e05ca7f38444b9f197ade1dbde2c0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653268B2

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