Methyl iodide → HCID 68671490, compound

Participants

Reaction Steps

To the sodium hydride (48 mg, 2 mmol) in THF (5 ml) at −78° C., (R)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate was slowly added. After 15 min, methyl iodide (0.124 ml, 2 mmol) was added and the reaction mixture was slowly allowed to come to rt overnight. Then the reaction mixture was quenched with MeOH and diluted with water (15 ml). Aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried over sodium sulfate and then filtered. The solvent was removed under vacuum, and the crude product was purified by silica gel chromatography (eluting with 15% EtOAc/hexanes) to afford (R)-tert-butyl 2-(methoxymethyl)pyrrolidine-1-carboxylate in 80% yield. (R)-2-(methoxymethyl)pyrrolidine was generated by removal of the Boc protecting group by treatment with trifluoroacetic acid.

Provenance & Evidence