Pyridine → HCID 58010302, compound

Temperature

0 °C

A flask was charged with (R)-tert-butyl pyrrolidin-3-ylcarbamate (1.0 g, 5.4 mmol, Lancaster) in DCM (15 mL) to give a colorless solution. Pyridine (0.89 mL, 10.8 mmol) was added and the solution was cooled to about 0° C., followed by the addition of triphosgene (0.64 g, 2.1 mmol). The mixture was stirred for about 1 h while slowly warming to ambient temperature. To the reaction solution was added DCM (50 mL) and the solution was washed with water (20 mL) and HCl (1N, 10 mL). The organic portion was separated, dried over anhydrous MgSO4, filtered, and concentrated to dryness under reduced pressure to give (R)-tert-butyl 1-(chlorocarbonyl)pyrrolidin-3-ylcarbamate (1.3 g, 98%) as a yellow oil: 1H NMR (DMSO-d6) δ 7.28 (s, 1 H), 4.03 (m, 1 H), 3.73-3.20 (m, 4 H), 2.05 (m, 1 H), 1.81 (m, 1 H), 1.39 (s, 9 H).

1. customto give a colorless solution
2. temperaturewhile slowly warming to ambient temperature
3. washthe solution was washed with water (20 mL) and HCl (1N, 10 mL)
4. customThe organic portion was separated
5. dry with materialdried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-b11626b700ff4999a863f5f79cde3f7e

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365579B2