Methyl iodide → (R)-tert-Butyl 3-methoxypyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

(3R)-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (12.5 g, 66.70 mmol) was dissolved in tetrahydrofuran (334 ml) and the reaction mixture cooled to 0° C. in an ice bath. The reaction mixture was treated with sodium hydride (2.20 g, 80% dispersion in mineral oil, 73.3 mmol) and allowed to warm to room temperature. The reaction mixture was then treated with methyl iodide (14.5 g, 100 mmol) and stirred at room temperature for 18 hours. The reaction mixture was diluted with water (100 ml) and concentrated in vacuo until just the aqueous remained. The aqueous was extracted with ethyl acetate (750 ml), the organic layer separated, dried (MgSO4) and concentrated in vacuo to yield the title product as a brown oil, 12.48 g.

Provenance & Evidence