Methylhydrazine → Tert-butyl 3-(aminooxy)pyrrolidine-1-carboxylate

HRID 1821817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821817
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1.CNN>C(Cl)Cl.CO>[NH2:3][O:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1

Komponenten

5

Edukt 2

HCID 6061MethylhydrazineHCID 19691445tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrrolidine-1-carboxylate

Produkt 1

HCID 19691331Tert-butyl 3-(aminooxy)pyrrolidine-1-carboxylateAusbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice-cold solution of tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrrolidine-1-carboxylate (0.96 g, 2.8 mmol) in CH2Cl2 (16 mL) and MeOH (4 mL) was added methylhydrazine (0.70 mL, 13 mmol) dropwise. The stirred reaction mixture was allowed to slowly warm to ambient temperature. After 2 h, the reaction mixture was concentrated under reduced pressure. To the residue was added CH2Cl2 (20 mL) and with the aid of sonication a solid formed and was collected by vacuum filtration. The filtrate was concentrated and purified by column chromatography (silica gel, 75:25 hexanes/EtOAc to 25:75 hexanes/EtOAc) to afford tert-butyl 3-(aminooxy)pyrrolidine-1-carboxylate (440 mg, 76%): 1H NMR (500 MHz, CDCl3) δ 1.46 (9H, s), 1.82-1.98 (1H, m), 2.04-2.10 (1H, m), 3.31-3.65 (4H, m), 4.24-4.27 (1H, m), 5.37.

Aufarbeitung

  1. customThe stirred reaction mixture
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added CH2Cl2 (20 mL)
  4. customwith the aid of sonication a solid
  5. customformed
  6. filtrationwas collected by vacuum filtration
  7. concentrationThe filtrate was concentrated
  8. custompurified by column chromatography (silica gel, 75:25 hexanes/EtOAc to 25:75 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-9e02d667f66a420995ec24c603a5c40c
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608627B2

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