反应 #51134

反应方程式

Carboxylic acid

3-[4-(methoxycarbonyl)bicyclo[2.2.2]oct-1-yl]propanoic acid

borane

HCl

→

methyl 4-(3-hydroxypropyl)bicyclo[2.2.2]octane-1-carboxylate

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   萃取extracted three times with 50 mL of methylene chloride
2. 2
   干燥The combined organic layers were dried over magnesium sulfate
3. 3
   其他the solvent was removed under reduced pressure

实验过程

Carboxylic acid 11-3 (400 mg, 1.67 mmol) was dissolved in tetrahydrofuran (5 mL) and borane (1 M solution in THF, 2.17 mL, 1.3 eq.) was added dropwise at room temperature. After 2 h the reaction was added to 50 mL of 1 N HCl and then extracted three times with 50 mL of methylene chloride. The combined organic layers were dried over magnesium sulfate and the solvent was removed under reduced pressure to afford crude methyl 4-(3-hydroxypropyl)bicyclo[2.2.2]octane-1-carboxylate (11-4) which was used without purification in the next step. 1H NMR (500 MHz, CD3OD): δ 3.66 (3H, s), 3.62 (2H, t, J=6.5 Hz), 1.78 (6H, m), 1.50 (2H, m), 1.41 (2H, m), 1.17 (2H, m) ppm.

来源