Methyl iodide → HCID 131731890, compound

Temperature

0 °C

To a solution of racemic (trans)-tert-butyl 3-(dimethylamino)-4-hydroxypyrrolidine-1-carboxylate (0.96 g, 4.17 mmol) in THF (40 mL) at 0° C. was added NaH (0.25 g, 6.25 mmol, 60% dispersion in mineral oil), and the reaction mixture was stirred at 0° C. for 10 min. Then, iodomethane (0.29 mL, 4.6 mmol) was added dropwise and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was quenched with sat aq NH4Cl and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to provide racemic-(trans)-tert-butyl-3-(dimethylamino)-4-methoxypyrrolidine-1-carboxylate. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.84 (br. s., 1 H), 3.46-3.54 (m, 1 H), 3.25 (s, 3 H), 3.12-3.22 (obs m, 3 H), 2.72 (br. s., 1 H), 2.16 (s, 6 H), 1.39 (s, 9 H).

1. stirringthe resulting mixture was stirred at room temperature for 18 h
2. customThe reaction mixture was quenched with sat aq NH4Cl
3. extractionextracted three times with EtOAc
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-5cd7a4ebf4ff49aab37b4fd6728e2d66

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846656B2