反応 #11678

反応方程式

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

hydrochloric acid

ethyl acetate

→

title compound

収率 19.0%

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

収率 19.0%

溶媒

borane

tetrahydrofuran

反応条件

後処理

1. 1
   温度After cooling to room temperature
2. 2
   workup.STIRRINGThis mixture was stirred for 3 h before the layers
3. 3
   その他were separated
4. 4
   洗浄The organic phase was washed with water (10 mL three times)
5. 5
   その他evaporated under vacuum
6. 6
   その他The residue was chromatographed on reverse phase preparative HPLC

実験手順

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.

出典