Reaction #1413

Reaction equation

pivalaldehyde

3-aminopyrrolidine

8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-3-quinolinecarboxylic acid

1,4-diazabicyclo[2.2.2]octane

3-(2,2-dimethylpropylideneamino)-pyrrolidine

→

7-(3-amino-1-pyrrolidinyl)-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Solvents

acetonitrile

acetonitrile

dimethylformamide

Conditions

Workup

1. 1
   Otherrises from 22.5° C. to 27.5° C
2. 2
   Otherthe reaction by gas chromatography
3. 3
   workup.ADDITIONare added
4. 4
   Temperaturethe mixture is heated
5. 5
   Temperatureunder reflux for 1 hour
6. 6
   OtherWork up gives the
7. 7
   Othersame result

Procedure

0.95 g (11 mmol) of pivalaldehyde are added dropwise to a solution of 0.86 g (10 mmol) of 3-aminopyrrolidine in 10 ml of acetonitrile at room temperature in the course of 5 minutes, during which the temperature rises from 22.5° C. to 27.5° C. The mixture is subsequently stirred for 1 hour and a virtually complete conversion into 3-(2,2-dimethylpropylideneamino)-pyrrolidine is found by checking the reaction by gas chromatography. The mixture is then diluted with 10 ml of acetonitrile and 10 ml of dimethylformamide, 3 g (10 mmol) of 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-3-quinolinecarboxylic acid and 2.2 g (20 mmol) of 1,4-diazabicyclo[2.2.2]octane are added and the mixture is heated under reflux for 1 hour. Work up gives the same result as described under Example 2a).

Source