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N-bromobutanimide → Tert-butyl 1'-(5-bromopyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

HRID 2093466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2093466
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH2:9][CH2:8]1.[Br:26]N1C(=O)CCC1=O>CN(C=O)C.[Cl-].[Na+].O>[Br:26][C:5]1[N:4]=[CH:3][C:2]([N:7]2[CH2:12][CH2:11][CH:10]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH2:9][CH2:8]2)=[N:1][CH:6]=1
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Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 54581959Tert-butyl 1'-pyrazin-2-yl-4,4'-bipiperidine-1-carboxylate

Produkt 1

HCID 59178948Tert-butyl 1'-(5-bromopyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

The tert-butyl 1′-pyrazin-2-yl-4,4′-bipiperidine-1-carboxylate (16 mg, 0.046 mmol, prepared as described for Example 8) and N-bromosuccinimide (8.2 mg, 0.046 mmol) were dissolved in DMF (0.2 ml) and the solution stirred overnight at 50 C. The slurry was diluted with 15% brine:water (40 ml) and extracted with ethyl acetate (3×25 ml). The combined organic fraction was washed with brine, dried over magnesium sulfate, filtered, and the volatiles removed in vac. The crude material was purified by chromatography on silica gel with 20% acetone:hexanes to yield the title compound.

Aufarbeitung

  1. extractionwater (40 ml) and extracted with ethyl acetate (3×25 ml)
  2. washThe combined organic fraction was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed in vac
  6. customThe crude material was purified by chromatography on silica gel with 20% acetone

Quellen und Nachweise

ORD-Eintrag
ord-a9b17a5298cc4bb3ae23c18e5b2970f5
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08445499B2

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