反应 #1880980

反应方程式

2-{(1R,2R,4R)-4-[6-(cyclopentylamino)purin-9-yl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}ethan-1-one

potassium-tert-butoxide

(bromomethyl)triphenylphosphonium bromide

→

{9-[4-((2E)-3-bromoprop-2-enyl)(2R,4R,5R)-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl]purin-6-yl}cyclopentylamine

溶剂

THF

tetrahydrofuran

反应条件

后处理

1. 1
   workup.ADDITIONwas added slowly
2. 2
   workup.STIRRINGthe mixture stirred under an atmosphere of N2 at −78° C. for 3 hours
3. 3
   其他brought to room temperature
4. 4
   workup.STIRRINGstirred for 4 days
5. 5
   其他The reaction mixture was quenched with saturated NH4Cl aqueous solution (15 mL)
6. 6
   workup.ADDITIONdiluted with H2O (60 mL)
7. 7
   萃取extracted with EtOAc (3×50 mL)
8. 8
   洗涤The combined organic layers were washed with H2O (2×50 mL)
9. 9
   干燥dried over Na2SO4
10. 10
    其他evaporated under reduced pressure

实验过程

To a stirred solution of potassium-tert-butoxide (0.78 g, 6.93 mmol) in tetrahydrofuran (45 mL) was added (bromomethyl)triphenylphosphonium bromide (1.51 g, 3.27 mmol) in small portions at −78° C. The resulting mixture was stirred at −78° C. for 2 hours. 2-{(1R,2R,4R)-4-[6-(cyclopentylamino)purin-9-yl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}ethan-1-one, a compound of Formula (11) (0.89 g, 2.31 mmol) dissolved in THF (15 mL) was added slowly and the mixture stirred under an atmosphere of N2 at −78° C. for 3 hours, brought to room temperature slowly and stirred for 4 days. The reaction mixture was quenched with saturated NH4Cl aqueous solution (15 mL) and diluted with H2O (60 mL), and then extracted with EtOAc (3×50 mL). The combined organic layers were washed with H2O (2×50 mL), dried over Na2SO4, and evaporated under reduced pressure, to provide {9-[4-((2E)-3-bromoprop-2-enyl)(2R,4R,5R)-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl]purin-6-yl}cyclopentylamine, a compound of formula (12), which was isolated by column chromatography.

来源