反应 #42725

反应方程式

methanol

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

tetrahydrofuran

Borane

→

title compound

收率 81.0%

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

收率 81.0%

溶剂

toluene

反应条件

后处理

1. 1
   浓缩The mixture was concentrated under vacuum
2. 2
   workup.DISSOLUTIONthe residue was dissolved
3. 3
   过滤filtered while hot and
4. 4
   温度then cooled to room temperature
5. 5
   过滤The crystals were filtered
6. 6
   洗涤washed with acetonitrile
7. 7
   其他dried under vacuum

实验过程

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).

来源