Hydrochloric Acid → HCID 131734317, compound

To a solution of L-Proline (1000 mg, 8.69 mmol) and sodium nitrite (845 mg, 12.2 mmol) in water 2.00 mL) cooled to 0° C. was slowly added concentrated hydrochloric acid (1.0 mL, 11.6 mmol). The reaction mixture was allowed to warm to room temp and stirred overnight. The reaction mixture was diluted with water and extracted with MTBE, dried over sodium sulfate and concentrated in vacuo. The crude residue was then taken up in toluene (4.00 mL) and cooled to 0° C. Trifluoroacetic anhydride (1.81 mL, 13.0 mmol) was then added and the reaction was stirred overnight at room temp. The reaction mixture was concentrated in vacuo, adsorbed onto silica and purified by column chromatography (0-10% MeOH in DCM) to afford the title compound as a brown oil (0.807 g, 74%)1H NMR (400 MHz, CDCl3) δ 4.43 (t, J=7.6 Hz, 2H), 2.96-2.86 (m, 2H), 2.85-2.73 (m, 2H). LC-MS (ESI): m/z=127.0 (M+H)+.

1. extractionextracted with MTBE
2. dry with materialdried over sodium sulfate
3. concentrationconcentrated in vacuo
4. temperaturecooled to 0° C
5. stirringthe reaction was stirred overnight at room temp
6. concentrationThe reaction mixture was concentrated in vacuo
7. custompurified by column chromatography (0-10% MeOH in DCM)

ORD record

ord-e9f136305dad458e91d06d196fe4fb08

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212186B2