反应 #742312

反应方程式

(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enol

pyridine

Ethyl chloroformate

→

title compound

Carbonic acid (1S,4R)-4-(2,6-dichloro-purin-9-yl)-cyclopent-2-enyl ester ethyl ester

溶剂

THF

反应条件

后处理

1. 1
   其他does not rise above 40° C.
2. 2
   其他The solvent is removed in vacuo
3. 3
   其他the residue is partitioned between dichloromethane (200 mL) and water (200 mL)
4. 4
   洗涤The organic layer is washed with water (150 mL) and brine (150 mL)
5. 5
   干燥dried over MgSO4
6. 6
   过滤filtered
7. 7
   其他the solvent is removed in vacuo

实验过程

(1S,4R)-4-(2,6-Dichloro-purin-9-yl)-cyclopent-2-enol [step 1](9.5 g, 35.05 mmol) is placed in an oven-dried flask under an atmosphere of argon. Dry THF (200 mL) is added followed by dry pyridine (5.54 g, 70.1 mmol). Ethyl chloroformate (15.21 g, 140.2 mmol) is added slowly so that the temperature does not rise above 40° C. and the reaction mixture is stirred at RT. The reaction is shown to be complete by LCMS after 2 hours. The solvent is removed in vacuo and the residue is partitioned between dichloromethane (200 mL) and water (200 mL). The organic layer is washed with water (150 mL) and brine (150 mL), dried over MgSO4, filtered and the solvent is removed in vacuo. The title compound is obtained after crystallization from methanol.

来源