Reacción #2195505

ord-e71af8df398141858e4518bc0f82dc60

Ecuación de reacción

CC(C)(C)[Si](C)(C)OC1CC(=O)OC(=O)C1
4-(tert-butyldimethylsilyloxy)dihydro-2H-pyran-2,6(3H)-dione
[NH4+].[OH-]
ammonium hydroxide
N
ammonia
→
CC(C)(C)[Si](C)(C)OC1CC(=O)NC(=O)C1
title compound
CC(C)(C)[Si](C)(C)OC1CC(=O)NC(=O)C1
4-(tert-Butyldimethylsilyloxy)piperidine-2,6-dione

Reactantes

CC(C)(C)[Si](C)(C)OC1CC(=O)OC(=O)C1
4-(tert-butyldimethylsilyloxy)dihydro-2H-pyran-2,6(3H)-dione
[NH4+].[OH-]
ammonium hydroxide
N
ammonia

Reactivos

Ninguno

Disolventes

C1COCCO1
dioxane

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaCool in an ice/water bath
  2. 2
    OtroCap the pressure tube
  3. 3
    TemperaturaCool the mixture
  4. 4
    Concentraciónconcentrate in vacuo
  5. 5
    OtroPurify the residue by silica gel chromatography

Procedimiento

Dissolve 4.1 mmol of 4-(tert-butyldimethylsilyloxy)dihydro-2H-pyran-2,6(3H)-dione (Nagao Y et al., Chem. Lett. 1990 9: 1503) in 10 mL of dioxane in a pressure tube. Cool in an ice/water bath, add 15 mL of saturated ammonium hydroxide and treat with gaseous ammonia via bubbler for about 10 min. Cap the pressure tube and heat in a 100° C. oil bath for 17 h. Cool the mixture and concentrate in vacuo. Purify the residue by silica gel chromatography using ethyl acetate/hexanes eluant to yield the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07514068B2uspto-grants-2009_04