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

Temperature

0 °C

tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate (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 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 treated 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. 1H NMR (CDCl3, 400 MHz) δ: 1.41 (s, 9H), 1.95 (m, 2H), 3.30 (s, 3H), 3.40 (m, 4H), 3.86 (m, 1H)

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

ORD record

ord-4a615ef010ee4e65bc36caa4162a93d3

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097621B2