反応 #51134

反応方程式

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

溶媒

tetrahydrofuran

反応条件

後処理

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

実験手順

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.

出典