Reaktion #162229

ord-906f4ef20f494d3b8c72e92acece46e4

Reaktionsgleichung

Cl
HCl
CCOC(=O)C(=O)N(C(=O)OC(C)(C)C)C1CC2CC(C(=O)OC)C1C2
methyl 6-[tert-butoxycarbonyl-(2-ethoxy-2-oxo-acetyl)amino]norbornane-2-carboxylate
[Na+].[OH-]
NaOH
→
CC(C)(C)OC(=O)NC1CC2CC(C(=O)O)C1C2
desired product
CC(C)(C)OC(=O)NC1CC2CC(C(=O)O)C1C2
6-(tert-butoxycarbonylamino)norbornane-2-carboxylic acid

Edukte

Cl
HCl
—
72f
CCOC(=O)C(=O)N(C(=O)OC(C)(C)C)C1CC2CC(C(=O)OC)C1C2
methyl 6-[tert-butoxycarbonyl-(2-ethoxy-2-oxo-acetyl)amino]norbornane-2-carboxylate
[Na+].[OH-]
NaOH

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted twice with EtOAc
  2. 2
    TrocknenThe combined organic phases were dried (Na2SO4)
  3. 3
    Filtrationfiltered
  4. 4
    Einengenconcentrated in vacuo

Vorschrift

To a solution of methyl 6-[tert-butoxycarbonyl-(2-ethoxy-2-oxo-acetyl)amino]norbornane-2-carboxylate, 72f, (0.80 g, 2.17 mmol) in methanol (20 mL) was added NaOH (4.33 mL of 2N solution, 8.66 mmol) at room temperature. The reaction mixture was stirred overnight. The mixture was diluted into 0.5 N HCl in ice, and extracted twice with EtOAc. The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo to afford 600 mg of desired product that was used without further purification.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08829007B2uspto-grants-2014_09