Reacción #712873

Ecuación de reacción

(1S,2S)-2-{4-[(R)-7-Fluoro-4-(4-hydroxy-phenoxy)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester

cesium carbonate

toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester

Intermediate 10

toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester

Intermediate 7

(1S,2S)-2-{4-[(R)-7-Fluoro-4-(4-hydroxy-phenoxy)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester

→

title compound

(1S,2S)-2-(4-{(R)-7-Fluoro-4-[4-(3-hydroxy-3-methyl-butoxy)-phenoxy]-indan-1-yloxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester

Disolventes

N,N-dimethylformamide

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water
2. 2
   Otrodried
3. 3
   Otrothe solvent removed
4. 4
   OtroThe residue is purified by flash chromatography (gradient of ethyl acetate in cyclohexane)

Procedimiento

(1S,2S)-2-{4-[(R)-7-Fluoro-4-(4-hydroxy-phenoxy)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester (Intermediate 7, 47 mg, 0.10 mmol), toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester (Intermediate 10, 54 mg, 0.21 mmol), and cesium carbonate (107 mg, 0.21 mmol) are suspended in dry N,N-dimethylformamide (2 mL) and stirred overnight. The mixture is diluted with ethyl acetate, washed with water, dried and the solvent removed. The residue is purified by flash chromatography (gradient of ethyl acetate in cyclohexane) to give the title compound. (Yield 60 mg). LC (METHOD 6): tR=0.75 min; Mass spectrum (ES+): m/z=535 [M+H]+.

Fuente