反応 #42725

反応方程式

methanol

8-Benzyloxy 5-(2-bromoacetyl)-1H-quinolin-2-one

tetrahydrofuran

Borane

→

title compound

収率 81.0%

8-Benzyloxy-5-((R)-2-bromo-1-hydroxyethyl)-1H-quinolin-2-one

収率 81.0%

溶媒

toluene

反応条件

後処理

1. 1
   濃縮The mixture was concentrated under vacuum
2. 2
   workup.DISSOLUTIONthe residue was dissolved
3. 3
   ろ過filtered while hot and
4. 4
   温度then cooled to room temperature
5. 5
   ろ過The crystals were filtered
6. 6
   洗浄washed with acetonitrile
7. 7
   その他dried under vacuum

実験手順

8-Benzyloxy 5-(2-bromoacetyl)-1H-quinolin-2-one (90.0 g, 243 mmol) was placed under nitrogen and tetrahydrofuran (900 mL) was added followed by the catalyst described above (1.8 M in toluene, 15 mL, 27 mmol). The suspension was cooled to −10±5° C. in an ice/isopropanol bath. Borane (1.0 M in THF, 294 mL, 294 mmol) was added over 4 h. The reaction was then stirred an additional 45 min at −10° C. and then methanol (250 mL) was added slowly. The mixture was concentrated under vacuum and the residue was dissolved in boiling acetonitrile (1.3 L), filtered while hot and then cooled to room temperature. The crystals were filtered, washed with acetonitrile and dried under vacuum to give the title compound (72.5 g, 196 mmol, 81% yield, 95% ee, 95% pure by HPLC).

出典