Hydrazine hydrate (1:1) → 3-(Aminooxy)-1-(diphenylmethyl)azetidine

HRID 82957

Reaktionsgleichung

Reaktionsgleichung von HRID 82957
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[CH2:11][CH:10]([O:12][N:13]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C>[NH2:13][O:12][CH:10]1[CH2:11][N:8]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:9]1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 683380242-{[1-(Diphenylmethyl)azetidin-3-yl]oxy}-1H-isoindole-1,3(2H)-dione

Produkt 1

HCID 671546883-(Aminooxy)-1-(diphenylmethyl)azetidineAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 2-{[1-(diphenylmethyl)azetidin-3-yl]oxy}-1H-isoindole-1,3(2H)-dione (600 mg, 1.56 mmol; which may be prepared as described in Step 2) in ethanol (13.3 mL) was added hydrazine hydrate (100 μL, 2.06 mmol). The resulting mixture was heated to reflux for 2 h then concentrated under reduced pressure. The residue was taken up in dichloromethane/methanol mixture then filtered. The filtrate was concentrated and the residue purified on column chromatography (eluent: Dichloromethane/NH3 7N in MeOH, 2% to 5%) to give the title compound (307 mg, 77%) as a clear oil.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationthen concentrated under reduced pressure
  4. filtrationthen filtered
  5. concentrationThe filtrate was concentrated
  6. customthe residue purified on column chromatography (eluent: Dichloromethane/NH3 7N in MeOH, 2% to 5%)

Quellen und Nachweise

ORD-Eintrag
ord-52f165fdeb534329a6963f6cf99ea443
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846711B2

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