Reacción #8731

ord-6bc67ca7fb6f48d4b4d2e9c4d8a61c2c

Ecuación de reacción

CN1CC[C@@H](Oc2cc([N+](=O)[O-])ccc2C(F)(F)F)C1
2-((R)-1-Methyl-pyrrolidin-3-yloxy)-4-nitrobenzotrifluoride
[H][H]
hydrogen
O=S(=O)([O-])[O-].[Mg+2]
magnesium sulfate
CN1CC[C@@H](Oc2cc(N)ccc2C(F)(F)F)C1
product
CN1CC[C@@H](Oc2cc(N)ccc2C(F)(F)F)C1
3-((R)-1-Methyl-pyrrolidin-3-yloxy)-4-trifluoromethyl-phenylamine

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Filtraciónthen filtered through a pad of Celite
  2. 2
    LavadoThe filter cake was rinsed with ethyl acetate (2×25 ml)
  3. 3
    Otrothe filtrate was evaporated under reduced pressure to an oil
  4. 4
    OtroThis oil was evaporated twice for dichloromethane (50 ml)
  5. 5
    Otroto remove

Procedimiento

A solution of 2-((R)-1-Methyl-pyrrolidin-3-yloxy)-4-nitrobenzotrifluoride (7.8 g, 26.9 mmol) in ethyl acetate (50 ml) was treated with 10% platinum on carbon (200 mg) then subjected to 40 psi hydrogen pressure for 3 hrs. The slurry was treated with anhydrous magnesium sulfate (5 g) then filtered through a pad of Celite. The filter cake was rinsed with ethyl acetate (2×25 ml) then the filtrate was evaporated under reduced pressure to an oil. This oil was evaporated twice for dichloromethane (50 ml) to remove trapped ethyl acetate. This gave the product as a clear light brown oil that solidified on standing (6.9 g, 99%): LCMS 249 (M++H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07091204B2uspto-grants-2006_08