反应详情

温度

150 °C

Sodium azide (0.94 g, 14.2 mmol) was added to a suspension of 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid 1,1-dimethylethyl ester (2.18 g, 10.9 mmol) and ammonium chloride (0.76 g, 14.2 mmol) in a mixture of EtOH (11 mL) and H2O (11 mL). The mixture was stirred at 150° C. for 5 minutes under microwave irradiation. Then a saturated solution of NaHCO3 was added and the mixture was extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in Heptane 20/80 to 80/20). The desired fractions were collected and the solvents evaporated in vacuo to yield 4-azido-3-hydroxy-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (0.93 g, 35% yield) and 3-azido-4-hydroxy-1-piperidinecarboxylic acid 1,1-dimethylethyl ester (0.26 g, 10% yield).

1. extractionthe mixture was extracted with DCM
2. customThe organic layer was separated
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. customthe solvent evaporated in vacuo
6. customThe crude product was purified by flash column chromatography (silica; AcOEt in Heptane 20/80 to 80/20)
7. customThe desired fractions were collected
8. customthe solvents evaporated in vacuo