反应详情

4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid methyl ester (2.05 g, 0.00398 mol) was dissolved in 100 mL of acetone and chilled in an ice-bath. To the solution was added Jones reagent (Prepared via the method of Feiser and Feiser) dropwise until a red color persisted. The reaction was allowed to warm to room temperature and then stirred for 18 hours at ambient temperature. The mixture was concentrated under vacuum to give a green solid. The residue was partitioned between ethyl acetate (150 mL) and water (150 mL). The organic layer was separated, washed with water (3×100 mL), brine (1×100 mL) and treated with MgSO4, filtered and concentrated in vacuo to give alight green solid. Purification via column chromatography yielded 1.25 g (61% yield) of the title compound as a white solid. MH+ 514.6.

1. temperaturechilled in an ice-bath
2. customPrepared via the method of Feiser and Feiser) dropwise until a red color
3. concentrationThe mixture was concentrated under vacuum
4. customto give a green solid
5. customThe residue was partitioned between ethyl acetate (150 mL) and water (150 mL)
6. customThe organic layer was separated
7. washwashed with water (3×100 mL), brine (1×100 mL)
8. additiontreated with MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give alight green solid
12. customPurification via column chromatography