Réaction #2358525

ord-f10c281bdefe427d9fde890ba1716872

Équation de réaction

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
Rendement 78.6%
CS(=O)(=O)c1cc(F)cc(OCCN)c1
2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethanamine
Rendement 78.6%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionextracted with ethyl acetate (2×100 ml)
  2. 2
    LavageThe combined organic phase was washed with brine (75 ml)
  3. 3
    Séchagedried (Na2SO4)
  4. 4
    Autreevaporated

Mode opératoire

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09120728B2uspto-grants-2015_09