Triphosgene → (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]hexahydropyrrolo[1,2-a]-pyrazine-2(1H)-carbonyl chloride

HRID 1184587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184587
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][NH:17][CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[Cl:20][C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][N:17]([C:21]([Cl:20])=[O:23])[CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 94429TriphosgeneHCID 86680449(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]octahydropyrrolo[1,2-a]pyrazine

Produkt 1

HCID 86680508(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]hexahydropyrrolo[1,2-a]-pyrazine-2(1H)-carbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of the product from Example 54F (73 mg, 0.28 mmol) in dichloromethane (2.5 mL) was added triphosgene (32 mg, 0.106 mmol), and the resulting mixture was stirred at ambient temperature for 16 hours. The mixture was diluted with dichloromethane (10 mL) and washed by 10% aqueous NaHCO3 solution (5 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the title compound.

Aufarbeitung

  1. washwashed by 10% aqueous NaHCO3 solution (5 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3c9feca74d4e4f61ad2d7cf7e1fe30b2
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669255B2

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