Methyl iodide → O1-tert-butyl O2-methyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate

Temperature

0 °C

4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (861 mg, 3.32 mmol) was dissolved in DCM (6.6 mL) then 2,6-di-tert-butyl-4-methylpyridine (1.023 g, 4.98 mmol) and AgOTf (938 mg, 3.65 mmol) were added. The reaction mixture was cooled to 0° C. and iodomethane (0.25 mL, 3.98 mmol) was added. After 4 min, the reaction mixture was diluted with DCM and it was filtered over elite. The filtrate was concentrated to a residue which was dissolved in diethyl ether. The organic solution was washed with 10% HCl and brine, then dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (20% to 80% EtOAc/Hex) to afford the title compound (479 mg, 53%).

1. filtrationwas filtered over elite
2. concentrationThe filtrate was concentrated to a residue which
3. dissolutionwas dissolved in diethyl ether
4. washThe organic solution was washed with 10% HCl and brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude residue was purified by silica column chromatography (20% to 80% EtOAc/Hex)

ORD record

ord-9ff2852cf0d5454cbd5ea9ccb6ec7c20

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841278B2