Acetic Acid → tert-butyl 5-(benzylamino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Temperatur

0 °C

To a solution of tert-butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (9.57 g, 42.5 mmol) in DCM (170 mL) were added BnNH2 (4.56 g, 42.5 mmol) and AcOH (2.55 g, 42.5 mmol) at 0° C. and the reaction mixture was stirred at 0° C. for 0.5 h. Then NaBH(OAc)3 (18.00 g, 85.0 mmol) was added to the above mixture and the resulting mixture was stirred at rt for another 20 h, then quenched with saturated NaHCO3 solution (142 mL), and extracted with DCM (250 mL×3). The combined organic phases were washed with brine (250 mL×3), dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc) to give the title compound as a yellow solid (7.44 g, 55.3%).

1. stirringthe resulting mixture was stirred at rt for another 20 h
2. customquenched with saturated NaHCO3 solution (142 mL)
3. extractionextracted with DCM (250 mL×3)
4. washThe combined organic phases were washed with brine (250 mL×3)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel column chromatography (EtOAc)

ORD-Eintrag

ord-ddcb9a4f0cdb4c9b8cf56bef73eaa338

Quelldatensatz

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09403801B2