Dichloromethane → HCID 89677012, Verbindung

HRID 2278252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2278252
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]=O)=[CH:4][CH:3]=1.[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.ClCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][N:14]2[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 595962316-Bromo-2-methylpyridine-3-carbaldehyde

Produkt 1

HCID 89677012HCID 89677012, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A 100 mL round-bottom flask was charged with 6-bromo-2-methylpyridine-3-carbaldehyde (2.50 g, 12.6 mmol, 1.00 equiv), tert-butyl piperazine-1-carboxylate (2.34 g, 12.6 mmol, 1.00 equiv), and dichloromethane (50 mL). The resulting solution was stirred for 30 min at room temperature. Sodium triacetoxyborohydride (8.00 g, 37.8 mmol, 3.00 equiv) was added. The resulting solution was stirred overnight at room temperature and then diluted with water (30 mL). The resulting mixture was extracted with dichloromethane (3×20 mL) and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (22/78) to provide 3.80 g (82% yield) of tert-butyl 4-[(6-bromo-2-methylpyridin-3-yl)methyl]piperazine-1-carboxylate as a white solid. LCMS (ESI, m/z): 370 [M+H]+.

Aufarbeitung

  1. stirringThe resulting solution was stirred overnight at room temperature
  2. extractionThe resulting mixture was extracted with dichloromethane (3×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (22/78)

Quellen und Nachweise

ORD-Eintrag
ord-7e2bdaed54024356a273c0dbcbcadef0
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133148B2

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