Methyl iodide → HCID 75488129, compound

To a solution of 1-(4-Formyl-phenyl)-azetidine-3-carboxylic acid (Preparation 8, 4 g, 19.51 mmol) in DMF (50 mL) was added potassium carbonate (4.04 g, 29.77 mmol) at 0° C. and allowed to stir for 10 minutes followed by addition of methyl iodide (2.77 g, 19.51 mmol) at 0° C. Resulting reaction mixture was stirred at room temperature for 2 hours under nitrogen atmosphere. After consumption of starting material, reaction mixture was quenched with ice cold water (150 mL) and extracted with EtOAc (3×150 mL). Combined organic layer was washed with water (2×300 mL), brine (250 mL), dried over sodium sulphate and evaporated under reduced pressure to afford brown colored semi solid (4.7 g, crude). Crude was purified by column chromatography on silica gel (100-200 mesh). Compound was eluted using 20% ethyl acetate in hexane to afford yellow semisolid (2.6 g, 61%). 1H NMR (400 MHz, CDCl3) δ: 3.58-3.62 (m, 1H), 3.76 (s, 3H), 4.15-4.22 (m, 4H), 6.42 (d, 2H, J=8.6 Hz), 7.72 (d, 2H, J=6.98 Hz), 9.74 (s, 1H); LC-MS (M+H): =220.20.

1. customResulting
2. customreaction mixture
3. stirringwas stirred at room temperature for 2 hours under nitrogen atmosphere
4. customAfter consumption of starting material, reaction mixture
5. customwas quenched with ice cold water (150 mL)
6. extractionextracted with EtOAc (3×150 mL)
7. washCombined organic layer was washed with water (2×300 mL), brine (250 mL)
8. dry with materialdried over sodium sulphate
9. customevaporated under reduced pressure
10. customto afford brown colored semi solid (4.7 g, crude)
11. customCrude was purified by column chromatography on silica gel (100-200 mesh)
12. washCompound was eluted

ORD record

ord-ff8957d0ce844095945db8fc5137d866

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09061013B2