反应详情

672 mg of NaBH4 are added, in portions, to a suspension of 5.09 g of 3-methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide in 90 ml of ethanol brought to 5° C. the reaction medium is stirred for 30 minutes at ambient temperature. 50 ml of water and 100 ml of ethyl acetate are added. The two phases are separated, and the aqueous phase is washed with twice 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of dichloromethane and acetone (95/5 to 80/20). 2.78 g of 5-methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine are obtained in the form of a brown oil.

1. custombrought to 5° C.
2. customThe two phases are separated
3. washthe aqueous phase is washed with twice 50 ml of ethyl acetate
4. dry with materialThe combined organic phases are dried over magnesium sulfate
5. filtrationfiltered
6. customevaporated
7. customPurification
8. washis carried out by flash chromatography on silica gel (40-63 μm), elution
9. additionbeing carried out with a mixture of dichloromethane and acetone (95/5 to 80/20)