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0 °C

To 699 mg (18.48 mmol) sodium borohydride in 20 mL dry THF under nitrogen, was added 1.15 g (5.74 mmol) (S)-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester and the reaction was cooled to 0° C., 1.72 g (6.78 mmol) iodine in 10 mL dry THF was added dropwise over 30 minutes, the reaction mixture was allowed to warm to room temperature, and was heated under reflux for 19 hours. The mixture was cooled to room temperature and 25 mL MeOH was added dropwise over 15 minutes. After evaporation of the solvent, 30 mL KOH (1 M) was added and the mixture was stirred at room temperature for 2 hours. The aqueous phase was extracted with DCM (2×75 mL) and the combined organic layers were washed with saturated brine (3×50 mL), then dried over MgSO4. After filtration, the solvent was evaporated to give the desired product, which was used for the next step without further purification.

1. temperatureto warm to room temperature
2. temperaturewas heated
3. temperatureunder reflux for 19 hours
4. temperatureThe mixture was cooled to room temperature
5. customAfter evaporation of the solvent, 30 mL KOH (1 M)
6. additionwas added
7. extractionThe aqueous phase was extracted with DCM (2×75 mL)
8. washthe combined organic layers were washed with saturated brine (3×50 mL)
9. dry with materialdried over MgSO4
10. filtrationAfter filtration
11. customthe solvent was evaporated