Benzyl Bromide → HCID 58557870, Verbindung

Temperatur

0 °C

To a solution of methyl 4-(tert-butoxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate (2.50 g, 8.82 mmol) in DMF (42 mL) at about 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.706 g, 17.6 mmol). The reaction mixture was stirred for about 30 min at about 0° C. and TBAI (0.652 g, 1.76 mmol) and benzyl bromide (2.10 mL, 17.7 mmol) were added. The reaction was warmed to ambient temperature and continued to stir for about 5 h. The solvent was removed under reduced pressure and the residue was taken up in DCM (50 mL) and water (30 mL). The layers were separated and the organic phase was washed with brine (30 mL), dried over anhydrous MgSO4, filtered and concd under reduced pressure. The resulting oil was purified by silica gel chromatography eluting with a gradient of 0-30% EtOAc in heptane to give methyl 4-(benzyl(tert-butoxycarbonyl)amino)bicyclo[2.2.2]octane-1-carboxylate (2.71 g, 82%) as a clear colorless oil: LC/MS (Table 1, Method b) Rt=3.09 min; MS m/z: 374 (M+H)+.

1. temperatureThe reaction was warmed to ambient temperature
2. stirringto stir for about 5 h
3. customThe solvent was removed under reduced pressure
4. customThe layers were separated
5. washthe organic phase was washed with brine (30 mL)
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. customThe resulting oil was purified by silica gel chromatography
9. washeluting with a gradient of 0-30% EtOAc in heptane

ORD-Eintrag

ord-b5c58510a59249318e485c8816a3b096

Quelldatensatz

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08426411B2