反应详情

4-Allyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (2.97 g, 10 mmol) was dissolved in iPrOH (50.0 mL) and H2O (10.0 mL). To this was added a aqueous solution of NaIO4 (4.68 g, 21.8 mmol) in water (40.0 mL), followed by addition of OsO4 (8.4 mg, crystals, in one portion) at rt. The solution was stirred at rt. After 30 min, milky cloudy formed. Stirring was continued overnight. TLC and LC/MS did not detect the SM, but it is still very milky. The reaction mixture was poured into ice water (20 mL) and EtOAc (30 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (3×15 mL). The combined extracts were washed with brine, and concentrated to dryness to get a liquid. The liquid was subject a reduced distillation to remove isopropanol. The remaining liquid was purified on a 50-g silica gel column, eluted with MeOH in DCM (0-5%). Note: the product is not UV active. Anisaldehyde visualization was used. The product fractions were collected and concentrated to yield 1.03 g (34% yield) of the title compound as a liquid.

1. custommilky cloudy formed
2. stirringStirring
3. waitwas continued overnight
4. customThe two layers were separated
5. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
6. washThe combined extracts were washed with brine
7. concentrationconcentrated to dryness
8. customto get a liquid
9. distillationa reduced distillation
10. customto remove isopropanol
11. customThe remaining liquid was purified on a 50-g silica gel column
12. washeluted with MeOH in DCM (0-5%)
13. customThe product fractions were collected
14. concentrationconcentrated