tert-Butyl 4-{1-[(benzoyloxy)carbonyl]piperidin-4-yl}-3-oxopiperazin-1-carboxylate → HCID 68416800, Verbindung

HRID 2366538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366538
[C:1]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH2:23][CH2:22][N:21]([C:24](OC(C)(C)C)=O)[CH2:20][C:19]2=[O:31])[CH2:14][CH2:13]1)=[O:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.ClCCl>[CH3:24][N:21]1[CH2:22][CH2:23][N:18]([CH:15]2[CH2:16][CH2:17][N:12]([C:10]([O:9][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:11])[CH2:13][CH2:14]2)[C:19](=[O:31])[CH2:20]1

Komponenten

4

Edukt 1

HCID 86615672tert-Butyl 4-{1-[(benzoyloxy)carbonyl]piperidin-4-yl}-3-oxopiperazin-1-carboxylate

Produkt 1

HCID 68416800HCID 68416800, VerbindungAusbeute 117,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

tert-Butyl 4-{1-[(benzoyloxy)carbonyl]piperidin-4-yl}-3-oxopiperazin-1-carboxylate (0.42 g) obtained in Example 12b) was dissolved in trifluoroacetic acid (1 mL) and dichloromethane (1 mL), and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated, toluene was added to the residue and it was concentrated again under reduced pressure. The residue was dissolved in dichloromethane (15 mL) and formalin (37%; 0.5 mL) was added. After the reaction mixture was stirred at room temperature for 2 hours, sodium triacetoxyborohydride (0.53 g) was added, and the mixture was stirred at room temperature for 15 hours. The reaction mixture was washed with an aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (0.38 g, quantitative) as a light yellow oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiontoluene was added to the residue and it
  3. concentrationwas concentrated again under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (15 mL)
  5. additionformalin (37%; 0.5 mL) was added
  6. additionsodium triacetoxyborohydride (0.53 g) was added
  7. stirringthe mixture was stirred at room temperature for 15 hours
  8. washThe reaction mixture was washed with an aqueous sodium bicarbonate solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e6846d793dff444dac2390870c8fe326
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697865B2

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