Reacción #2358525

ord-f10c281bdefe427d9fde890ba1716872

Ecuación de reacción

CC(C)(C)OC(=O)NCCOc1cc(F)cc(S(C)(=O)=O)c1
tert-butyl 2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl-carbamate
Cl
HCl
[Na+].[OH-]
NaOH
CS(=O)(=O)c1cc(F)cc(OCCN)c1
title compound
Rendimiento 78.6%
CS(=O)(=O)c1cc(F)cc(OCCN)c1
2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethanamine
Rendimiento 78.6%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónextracted with ethyl acetate (2×100 ml)
  2. 2
    LavadoThe combined organic phase was washed with brine (75 ml)
  3. 3
    Secadodried (Na2SO4)
  4. 4
    Otroevaporated

Procedimiento

A mixture of tert-butyl 2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl-carbamate (1.4 g, 4.2 mmol) in EtOH (18 ml) was added HCl (1.25 M in EtOH, 6 ml). The mixture was stirred at ambient temperature for 20 h. The aqueous phase was made basic by addition of aqueous NaOH (1 M, 50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic phase was washed with brine (75 ml), dried (Na2SO4) and evaporated to yield the title compound (0.77 g, 77%). MS m/z (relative intensity, 70 eV 298 (M+, 18), 296 (M+, 18), 109 (bp), 107 (99), 82 (15).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09120728B2uspto-grants-2015_09