Reaction #11678

Reaction equation

(S)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

hydrochloric acid

ethyl acetate

→

title compound

Yield 19.0%

(S)-1-(2-hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

Yield 19.0%

Solvents

borane

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature
2. 2
   workup.STIRRINGThis mixture was stirred for 3 h before the layers
3. 3
   Otherwere separated
4. 4
   WashThe organic phase was washed with water (10 mL three times)
5. 5
   Otherevaporated under vacuum
6. 6
   OtherThe residue was chromatographed on reverse phase preparative HPLC

Procedure

A mixture of (S)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 10) (6 mg) in 1.0 M borane in tetrahydrofuran solution (2 mL) under argon was stirred at 35° C. for 3 h. After cooling to room temperature, 1.0 M aqueous hydrochloric acid (10 mL) and ethyl acetate (10 mL) were added. This mixture was stirred for 3 h before the layers were separated. The organic phase was washed with water (10 mL three times) and evaporated under vacuum. The residue was chromatographed on reverse phase preparative HPLC to isolate the title compound (1.1 mg) and the over-reduction product (S)-1-(2-hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-1,2,3,4-tetrahydroquinoline (0.9 mg). Title compound HPLC/MS [M+H]+, 384.

Source