반응 #11678

반응 방정식

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

hydrochloric acid

ethyl acetate

→

title compound

수율 19.0%

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

수율 19.0%

용매

borane

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

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