Reaktion #966

ord-ecbc4c566e744d9b960cfaf350b242df

Reaktionsgleichung

CC(C)(C)OC(=O)NCC1CN(C(c2ccccc2)c2ccccc2)C1
3-(N-tert-butyloxycarbonylaminomethyl)-1-benzhydryl azetidine
→
CC(C)(C)OC(=O)NCC1CNC1
title compound
Ausbeute 67.1%
CC(C)(C)OC(=O)NCC1CNC1
3-(N-tert-butyloxycarbonylaminomethyl) azetidine
Ausbeute 67.1%

Edukte

CC(C)(C)OC(=O)NCC1CN(C(c2ccccc2)c2ccccc2)C1
3-(N-tert-butyloxycarbonylaminomethyl)-1-benzhydryl azetidine

Reagenzien

[OH-].[OH-].[Pd+2]
Pd(OH)2

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe catalyst was filtered off
  2. 2
    Sonstigethe solvent evaporated
  3. 3
    SonstigeThe crude product was purified by flash chromatography

Vorschrift

3.4 g (9.6 mmol) of 3-(N-tert-butyloxycarbonylaminomethyl)-1-benzhydryl azetidine was dissolved in 170 mL MeOH and hydrogenated over 0.30 g Pd(OH)2 at 5 MPa over night. The catalyst was filtered off and the solvent evaporated. The crude product was purified by flash chromatography using MeOH/CH2Cl2, 1/9, followed by MeOH (saturated with NH3 (g))/CH2Cl2, 1/9, as eluent to yield 1.2 g (67%) of the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723444uspto-grants-1998_03