Reaktion #2127137

ord-379f006fe207490ba0df59115c23d1fb

Reaktionsgleichung

CN(C(=O)OC(C)(C)C)[C@H](CN=[N+]=[N-])C[C@H]1CCCOC1
tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate
[H][H]
hydrogen
→
CN(C(=O)OC(C)(C)C)[C@H](CN)C[C@H]1CCCOC1
tert-Butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate

Edukte

CN(C(=O)OC(C)(C)C)[C@H](CN=[N+]=[N-])C[C@H]1CCCOC1
tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate
[H][H]
hydrogen

Reagenzien

[Pd]
Pd/C

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe flask fitted with a gas inlet
  2. 2
    SonstigeThe flask was evacuated
  3. 3
    workup.ADDITIONback-filled with H2 from the balloon
  4. 4
    SonstigeThe catalyst was removed by filtration through a pad of Celite
  5. 5
    Sonstigethe mixture evaporated

Vorschrift

The tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate (2.1 g, 7.04 mmol, 1.0 equiv) and Pd/C (10%, ˜200 mg) were added to a flask. THF (30 mL) was added and the flask fitted with a gas inlet connected to a balloon of hydrogen gas. The flask was evacuated and back-filled with H2 from the balloon. This was repeated twice and the reaction mixture stirred for 17 h at ambient temperature. Analysis by LC/MS showed complete conversion to the desired amine. The catalyst was removed by filtration through a pad of Celite and the mixture evaporated. This provided 1.82 g (94%) of tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08580823B2uspto-grants-2013_11