Reacción #162165

ord-0d4cc5c0d6c04e548c25f4d3037b9914

Ecuación de reacción

[H][H]
hydrogen
[N-]=[N+]=[N-]
azide
CC(C)(C)[Si](C)(C)O[C@]1(C)CCC[C@H](N=[N+]=[N-])[C@H]1O
50d
CC(C)(C)[Si](C)(C)O[C@]1(C)CCC[C@H](N=[N+]=[N-])[C@H]1O
(1R,2R,3S)-3-azido-1-(tert-butyldimethylsilyloxy)-1-methylcyclo-hexan-2-ol
→
CC(C)(C)[Si](C)(C)O[C@]1(C)CCC[C@H](N)[C@H]1O
oil
CC(C)(C)[Si](C)(C)O[C@]1(C)CCC[C@H](N)[C@H]1O
(1R,2R,3S)-3-amino-1-(tert-butyldimethylsilyloxy)-1-methylcyclohexan-2-ol

Reactantes

[H][H]
hydrogen
[N-]=[N+]=[N-]
azide
CC(C)(C)[Si](C)(C)O[C@]1(C)CCC[C@H](N=[N+]=[N-])[C@H]1O
50d
CC(C)(C)[Si](C)(C)O[C@]1(C)CCC[C@H](N=[N+]=[N-])[C@H]1O
(1R,2R,3S)-3-azido-1-(tert-butyldimethylsilyloxy)-1-methylcyclo-hexan-2-ol

Reactivos

[Pd]
palladium

Disolventes

CCOC(C)=O
ethyl acetate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe reaction mixture was filtered over celite
  2. 2
    Lavadothe celite was eluted with 2×10 mL of EtOAc
  3. 3
    ConcentraciónThe filtrate was concentrated in vacuo

Procedimiento

A solution of azide, 50d, (0.25 g; 0.89 mmol) in 20 mL of ethyl acetate was hydrogenated with Degussa palladium (20 mole %) under 1 atmosphere of hydrogen overnight. The reaction mixture was filtered over celite and the celite was eluted with 2×10 mL of EtOAc. The filtrate was concentrated in vacuo to afford 230 mg of an oil that was used directly for the next step without further purification.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08829007B2uspto-grants-2014_09