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

Temperature

0 °C

(3R)-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (12.59, 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 80% sodium hydride in mineral oil (2.20 g, 73.3 mmol) and stirred until back at room temperature. The reaction mixture was then treated with methyl iodide (14.5 g, 100.0 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 solution was extracted with ethyl acetate (750 mL), the organic layer separated, dried over magnesium sulphate and concentrated in vacuo to yield the title product as a brown oil, 12.48 g.

1. stirringstirred at room temperature for 18 hours
2. concentrationconcentrated in vacuo until just the
3. extractionThe aqueous solution was extracted with ethyl acetate (750 mL)
4. customthe organic layer separated
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated in vacuo

ORD record

ord-1d3711da1449439e9b385e2429355c64

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569572B2