Dichloromethane → tert-Butyl 4-((4-bromofuran-2-yl)methyl)piperazine-1-carboxylate

HRID 2190260

Reaktionsgleichung

Reaktionsgleichung von HRID 2190260
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[O:5][CH:6]=1.C(Cl)Cl.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)[O:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27570104-Bromo-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 86699373tert-Butyl 4-((4-bromofuran-2-yl)methyl)piperazine-1-carboxylateAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-bromofuran-2-carbaldehyde (500 mg, 2.85 mmol) and CH2Cl2 (10 mL) was added tert-butyl piperazine-1-carboxylate (1.06 g, 5.74 mmol) and sodium triacetoxyborohydride (1.2 g, 5.74 mmol). The mixture was stirred at room temperature overnight. The resultant mixture was diluted with EtOAc (100 mL), washed with brine then dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2) to afford the sub-title compound (900 mg, 91%).

Aufarbeitung

  1. washwashed with brine
  2. dry with materialthen dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-9bea93ff56444fe3a645c33854574258
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324264B1

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