1-Methylpyrrolidine → HCID 90312005, compound

Temperature

90 °C

To a stirred solution of tert-butyl acrylate (9.99 g, 78.1 mmol, 3.50 equiv.), Et3N (8.5 mL, 60.2 mmol, 2.70 equiv.), N-methyl pyrrolidine (20 mL), Tritolylphosphine (1.17 g, 3.52 mmol, 0.16 equiv.) followed by Pd(OAc)2 (0.50 g, 2.22 mmol, 0.09 equiv.) were added. The temperature was gradually raised to 90° C. and compound 2 (5.00 g, 22.3 mmol, 1.0 equiv.) in NMP (10 mL) was added drop wise and stirred at 90° C. for 12 h. After consumption of the starting material (by TLC), the reaction mixture was filtered through pad of celite and washed with EtOAc (50 mL). The combined filtrate was washed with cold water (2×50 mL) followed by NaOCl (50 mL), brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude residue which was purified by column chromatography (3% EtOAc/hexane) to afford compound 3 (4.0 g, 66%) as yellow solid.

1. additionwere added
2. customAfter consumption of the starting material (by TLC)
3. filtrationthe reaction mixture was filtered through pad of celite
4. washwashed with EtOAc (50 mL)
5. washThe combined filtrate was washed with cold water (2×50 mL)
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto give the crude residue which
10. customwas purified by column chromatography (3% EtOAc/hexane)

ORD record

ord-f9b74f440f5e4adf97d54eb2a45ee15a

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901144B2