Methyl iodide → Tert-butyl 3-methoxypyrrolidine-1-carboxylate

To a stirred solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (0.5 g, 2.67 mmol) in THF (20 mL) at 0° C. was added NaH (60%, 0.077 g, 3.2 mmol) and the mixture was stirred for 15 min. Methyl iodide (0.2 mL, 3.2 mmol) was slowly added and the reaction was stirred for 18 h at ambient temperature. The reaction was quenched with water (5 mL) and extracted with DCM (3×10 mL). The combined organic extracts were washed with water (6 mL), brine (8 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by FCC eluting with DCM to afford the title compound.

1. stirringthe reaction was stirred for 18 h at ambient temperature
2. customThe reaction was quenched with water (5 mL)
3. extractionextracted with DCM (3×10 mL)
4. washThe combined organic extracts were washed with water (6 mL), brine (8 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified by FCC
8. washeluting with DCM

ORD record

ord-b213378f5ab44289871e3aff564c0a36

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623859B2