Borane;tetrahydrofuran → Tert-butyl 3-((pyridin-3-ylamino)methyl)piperazine-1-carboxylate

HRID 70232

Reaktionsgleichung

Reaktionsgleichung von HRID 70232
B.C1COCC1.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([CH:16]2[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)=O)[CH:8]=1>C1COCC1>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][CH2:14][CH:16]2[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH:8]=1

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 59671553Tert-butyl 3-(pyridin-3-ylcarbamoyl)piperazine-1-carboxylate

Produkt 1

HCID 59671589Tert-butyl 3-((pyridin-3-ylamino)methyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Borane-THF complex (1.0 M solution in THF, 3.4 mL, 3.4 mmol) was added to a solution of tert-butyl 3-(pyridin-3-ylcarbamoyl)piperazine-1-carboxylate (522 mg, 1.70 mmol) in THF (4 mL). The reaction mixture was heated to reflux for 5 h. Upon cooling to rt, the reaction mixture was carefully quenched by the dropwise addition of MeOH. After gas evolution ceased, MeOH (10 mL) was added, and the reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure, yielding the title compound which was used without further purification. LC-MS: RT=2.90 min, [M+H]+=293.1.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. customthe reaction mixture was carefully quenched by the dropwise addition of MeOH
  4. additionMeOH (10 mL) was added
  5. temperaturethe reaction mixture was heated
  6. temperatureto reflux overnight
  7. temperatureUpon cooling to rt
  8. concentrationthe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fa00b21b9f744c02a7a0d1a7d17a6886
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822472B2

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