Reaktion #51134

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle