Reaction #51134

Reaction equation

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

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionextracted three times with 50 mL of methylene chloride
2. 2
   DryingThe combined organic layers were dried over magnesium sulfate
3. 3
   Otherthe solvent was removed under reduced pressure

Procedure

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.

Source