HCID 78145418, compound → HCID 126634529, compound

Participants

Reaction Steps

A suspension of (4aSR*,5RS*,10bSR*)-5-cyclohexyl-10-nitro-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline (Example 12, obtained according to example 1 procedure) (90.0 mg, 0.284 mmol) and palladium on activated carbon (10 wt %, 34.5 mg, 0.031 mmol) in EtOH (10 mL) was purged with nitrogen followed by evacuation (three cycles) and then pressurized to 50 psi with hydrogen for 1 day while stirring. After the pressure was released, the reaction mixture was purged with nitrogen. The suspension was filtered over celite and the solvent removed under reduced pressure. The remaining residue was purified by Combiflash chromatography (SiO2, c-Hexane/AcOEt) to afford (4aSR*,5RS*,10bSR*)-5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-10-amine (21.4 mg, 26%) as yellow solid.

Provenance & Evidence