Reaction #2329019

Reaction equation

isobutyric acid chloride

(R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol

→

Fesoterodine

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Temperaturecooling by ice bath
2. 2
   OtherA white substance precipitated after approximately 5 minutes
3. 3
   workup.ADDITIONFor this purpose, drops of a solution of 17.7 g triethylamine in 250 ml dichloromethane were added in 5 minutes under agitation and ice bath
4. 4
   Temperaturecooling
5. 5
   WashThe batch was washed once with each of 250 ml water, 250 ml approximate 5% aqueous NaHCO3 solution and 250 ml water
6. 6
   ExtractionThe dichloromethane extract
7. 7
   Dryingdried over Na2SO4
8. 8
   Otherwas evaporated to a low small bulk on a rotary evaporator to constant weight, whereby a sallow, high viscosity oil
9. 9
   workup.WAITwas left

Procedure

Drops of a solution of 18.6 g isobutyric acid chloride in 250 ml dichloromethane were added in approximately 10 minutes to a solution of 59.8 g (175.1 mol) (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol cooled to −3° C. (A, see FIG. 1) dissolved in 750 ml dichloromethane with agitation and cooling by ice bath. A white substance precipitated after approximately 5 minutes. For this purpose, drops of a solution of 17.7 g triethylamine in 250 ml dichloromethane were added in 5 minutes under agitation and ice bath cooling. The batch was washed once with each of 250 ml water, 250 ml approximate 5% aqueous NaHCO3 solution and 250 ml water. The dichloromethane extract dried over Na2SO4 was evaporated to a low small bulk on a rotary evaporator to constant weight, whereby a sallow, high viscosity oil was left. Raw yield: 63.7 g (88.5% of the theory).

Source