Pyridine → HCID 86690247, Verbindung

HRID 80754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80754
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH3:15][C:16](OC(C)=O)=[O:17].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[C:16]([N:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[C@H:2]([CH3:1])[CH2:7]1)(=[O:17])[CH3:15]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10262201tert-Butyl (2R)-2-methylpiperazine-1-carboxylate

Produkt 1

HCID 86690247HCID 86690247, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (R)-tert-butyl 2-methylpiperazine-1-carboxylate (4.8 g, 23.97 mmol), Ac2O (3.39 mL, 36.0 mmol) and pyridine (3.88 mL, 47.9 mmol) in DCM (30 mL) was stirred at rt for 30 min. Reaction was diluted with EtOAc, washed with diluted HCl, brine and sat NaHCO3, brine, and dried over Na2SO4, concentrated. Resulting residue was treated with 1N NaOH in ether, extracted with ether, washed with brine, dried over Na2SO4, concentrated and purified by FCC (0-10% MeOH in DCM) to give (R)-tert-butyl 4-acetyl-2-methylpiperazine-1-carboxylate. 1H NMR (400 MHz, CD2Cl2) δ ppm 4.14-4.46 (m, 2 H) 3.74-3.91 (m, 1 H) 3.46-3.72 (m, 1 H) 2.92-3.35 (m, 2 H) 2.56-2.91 (m, 1 H) 2.05 (d, J=16.67 Hz, 3 H) 1.44 (s, 9 H) 1.03-1.18 (m, 3 H). MS (ESI+) m/z 243.2 (M+H)+.

Aufarbeitung

  1. customReaction
  2. washwashed with diluted HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. additionResulting residue was treated with 1N NaOH in ether
  6. extractionextracted with ether
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. custompurified by FCC (0-10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-bc8910e6209f469f9b626f2ce285e8bc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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