3-(4-(Pyrrolidin-1-yldiazenyl)phenyl)oxetan-3-ol → 3-(4-Aminophenyl)oxetan-3-ol

HRID 522667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 522667
N1(N=[N:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3([OH:18])[CH2:17][O:16][CH2:15]3)=[CH:10][CH:9]=2)CCCC1>CO.[Pd]>[NH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([OH:18])[CH2:15][O:16][CH2:17]2)=[CH:12][CH:13]=1

Komponenten

4

Edukt 1

HCID 1180225443-(4-(Pyrrolidin-1-yldiazenyl)phenyl)oxetan-3-ol

Produkt 1

HCID 575703463-(4-Aminophenyl)oxetan-3-olAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 3-(4-(pyrrolidin-1-yldiazenyl)phenyl)oxetan-3-ol (500 mg, 2.02 mmol) in methanol (15 mL) was added Pd/C (10%, 250 mg) at RT. The reaction mixture was stirred under 1 atm H2 atmosphere (balloon) at 40° C. for 18 h. The mixture was filtered through a pad of Celite. The filtrate was concentrated to give a residue, which was purified by Prep-HPLC to afford the title compound (200 mg, yield 60%) as a white solid. MS (ES+) C9H11NO2 requires: 165, found 166 [M+H]+, purity: 96%.

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. customto give a residue, which
  4. customwas purified by Prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d3af1d27ee514c4fab8b92baa4403be9
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334263B2

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