Sodium Hydroxide → (3R,4R)-tert-butyl 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-methyl-piperidine-1-carboxylate

HRID 1969731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969731
[CH3:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@@H:3]1[C:15]1[N:19]2[C:20]3[CH:26]=[CH:25][N:24](S(C4C=CC(C)=CC=4)(=O)=O)[C:21]=3[N:22]=[CH:23][C:18]2=[CH:17][N:16]=1.[OH-].[Na+]>O1CCOCC1>[C:15]1([C@@H:3]2[C@H:2]([CH3:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:4]2)[N:19]2[C:20]3[CH:26]=[CH:25][NH:24][C:21]=3[N:22]=[CH:23][C:18]2=[CH:17][N:16]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 58557067(3R,4R)-tert-butyl 4-methyl-3-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 58557258(3R,4R)-tert-butyl 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-methyl-piperidine-1-carboxylateAusbeute 108,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (3R,4R)-tert-butyl 4-methyl-3-(6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidine-1-carboxylate (40 g, 78 mmol) in 1,4-dioxane (160 mL) was added NaOH (1 N aqueous, 157 mL). The mixture was heated at about 60° C. for about 1 h. The mixture was allowed to cool to ambient temperature. The mixture was partitioned with HCl (4 N aqueous, 50 mL) and extracted with DCM (2×300 mL). The combined organic extracts were washed with brine (400 mL), dried over anhydrous Na2SO4, filtered then coned in vacuo. The product was purified on silica gel (330 g) using 1-5% MeOH in DCM to give (3R,4R)-tert-butyl 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-methylpiperidine-1-carboxylate (30 g, 99%): LC/MS (Table 1, Method b) Rt=2.00 min; MS m/z: 356 (M+H)+.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. customThe mixture was partitioned with HCl (4 N aqueous, 50 mL)
  3. extractionextracted with DCM (2×300 mL)
  4. washThe combined organic extracts were washed with brine (400 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe product was purified on silica gel (330 g)

Quellen und Nachweise

ORD-Eintrag
ord-000d9b8a2c4c4c169baed5d5281256db
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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