Methyl iodide → HCID 86639454, compound

Temperature

0 °C

To a solution of tert-butyl (S)-1-azido-3-((S)-oxepan-3-yl)propan-2-ylcarbamate (83 mg, 0.28 mmol) in anhydrous THF (5 mL) at −78° C. was added 1.0 M LHMDS solution in THF (1.1 mL, 1.12 mmol), then stirred at this temperature for 30 min. To this mixture was added MeI (237 mg, 104 μL, 1.67 mmol), then the temperature was allowed to warm to 0° C., and stand for 12 h and −20° C. The reaction mixture was quenched with saturated aq. NH4Cl, extracted with EtOAc (30 mL), the separated organic phase was washed with H2O (2×10 mL), brine, and dried over Na2SO4, and filtered. The filtrate was concentrated, the resulting slurry was purified through flash chromatography on silica gel (eluted with gradient system, 0-30% EtOAc in hexane) to afford tert-butyl (S)-1-azido-3-((S)-oxepan-3-yl)propan-2-yl(methyl)carbamate. MS ESI +ve m/z 321 (M+Na).

1. waitstand for 12 h and −20° C
2. customThe reaction mixture was quenched with saturated aq. NH4Cl
3. extractionextracted with EtOAc (30 mL)
4. washthe separated organic phase was washed with H2O (2×10 mL), brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationThe filtrate was concentrated
8. customthe resulting slurry was purified through flash chromatography on silica gel (eluted with gradient system, 0-30% EtOAc in hexane)

ORD record

ord-9be8d1569f4c4c5fb75d956866a6ab54

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08487108B2