Sodium hydride → HCID 86722318, compound

To a stirred solution of tert-butyl (3,3-diethoxypropyl)carbamate (1.0 g, 4.05 mmol) in DMF (15 mL) was added sodium hydride (0.25 g, 6.25 mmol). The reaction mixture was stirred at room temperature for 30 minutes and 3-methoxybenzyl bromide (0.875 mL, 6.25 mmol) added. The reaction mixture was stirred at room temperature for 72 hours. The reaction mixture was diluted with ethyl acetate and washed with water and twice with brine. The organic phase was dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was dissolved in ethanol (10 mL) and 4M hydrogen chloride in dioxane (10 mL) added. The reaction mixture was stirred at room temperature for 2 hours and the solvent evaporated at reduced pressure. The residue was loaded onto an SCX-2 cartridge and eluted with ethanol (4 column volumes) and then 10% triethylamine/ethanol (4 column volumes). The product containing fractions were combined and the solvent evaporated at reduced pressure to afford the title compound (0.543 g, 50%).

1. stirringThe reaction mixture was stirred at room temperature for 72 hours
2. washwashed with water and twice with brine
3. dry with materialThe organic phase was dried (magnesium sulfate)
4. filtrationfiltered
5. customthe solvent evaporated at reduced pressure
6. dissolutionThe residue was dissolved in ethanol (10 mL)
7. addition4M hydrogen chloride in dioxane (10 mL) added
8. stirringThe reaction mixture was stirred at room temperature for 2 hours
9. customthe solvent evaporated at reduced pressure
10. washeluted with ethanol (4 column volumes)
11. additionThe product containing fractions
12. customthe solvent evaporated at reduced pressure

ORD record

ord-4704b7fdf21d49429bf23192b12a0ab5

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08980913B2