反应详情

3-Amino-5-(4-octylphenyl)tetrahydrofuran-3-carboxylic acid (0.246 g, 0.770 mmol) was dissolved in THF (15.40 ml). A solution of lithium aluminum hydride (0.770 ml, 1.540 mmol) (Aldrich) was added carefully and the reaction stirred for about 3 h. The reaction was quenched by addition of water (60 uL) and stirred for about 30 min. 10% NaOH (180 uL) was added and the reaction stirred for about 1 h. Finally, water (60 uL) was added and the reaction stirred overnight. The mixture was filtered through Celite® and the solvents removed under reduced pressure. The residue was purified by flash column chromatography (0.5″×7″ of silica) eluting with 10% MeOH in methylene chloride and the product fractions combined. The solvents were removed under reduced pressure to provide (3-amino-5-(4-octylphenyl)tetrahydrofuran-3-yl)methanol (0.1 g, 0.327 mmol, 42.5% yield) as a colorless oil: LC/MS (method A) Rt=3.12 min.; MS m/z: 306.42 (M+H)+.

1. customThe reaction was quenched by addition of water (60 uL)
2. stirringstirred for about 30 min
3. addition10% NaOH (180 uL) was added
4. stirringthe reaction stirred for about 1 h
5. additionFinally, water (60 uL) was added
6. stirringthe reaction stirred overnight
7. filtrationThe mixture was filtered through Celite®
8. customthe solvents removed under reduced pressure
9. customThe residue was purified by flash column chromatography (0.5″×7″ of silica)
10. washeluting with 10% MeOH in methylene chloride
11. customThe solvents were removed under reduced pressure