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To a stirred emulsion of 53.8 parts of ethyl 7-oxa-3-azabicyclo-[4.1,0]heptane-3-carboxylate, 17.6 parts of ethanol and 195 parts of water were added portionwise, during a 15 minutes-period, 28.6 parts of sodium azide while cooling in an ice bath. The mixture was warmed slowly to room temperature and stirring was continued overnight at room temperature. The aqueous phase was separated and extracted twice with dichloromethane. The combined organic phases were washed with a small amount of water, dried, filtered and evaporated, yielding 56.3 parts (82%) of a mixture of 80% of ethyl trans- 4-azido-3-hydroxy-1-piperidinecarboxylate (interm. 3) and 15% of ethyl trans-3-azido-4-hydroxy-1-piperidinecarboxylate.

1. temperaturewhile cooling in an ice bath
2. customThe aqueous phase was separated
3. extractionextracted twice with dichloromethane
4. washThe combined organic phases were washed with a small amount of water
5. customdried
6. filtrationfiltered
7. customevaporated