Tetrahydrofuran → HCID 49872234, compound

Temperature

-78 °C

(S)-3-Formylpyrrolidine-1-carboxylic acid t-butyl ester (10.0 g, 50.2 mmol) and THF (100 mL, 1000 mmol) were combined under nitrogen, and the resulting solution was cooled to −78° C. 2.0M isopropylmagnesium chloride in THF (30.1 mL, 60.2 mmol) was then added dropwise over 10 minutes. The mixture was allowed to warm to room temperature slowly overnight. Then saturated aqueous NH4Cl (100 mL) was added dropwise to quench the reaction. The THF was removed under vacuum and the resulting mixture was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with saturated aqueous NaCl (1×100 mL), then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by normal phase chromatography (300 g SiO2, 12 g crude, 50-60% diethyl ether in hexanes) to yield the following as clear oils:

1. temperatureto warm to room temperature slowly overnight
2. customto quench
3. customthe reaction
4. customThe THF was removed under vacuum
5. extractionthe resulting mixture was extracted with EtOAc (2×100 mL)
6. washthe combined organic layers were washed with saturated aqueous NaCl (1×100 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by normal phase chromatography (300 g SiO2, 12 g crude, 50-60% diethyl ether in hexanes)
11. customto yield the following as clear oils

ORD record

ord-2cc800be205b4a7da6b671aad08022a7

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994209B2