HCID 78145418, compound → HCID 126634529, compound

HRID 717904Notes

Reaction equation

HRID 717904 reaction equation
[CH:1]1([CH:7]2[CH:16]3[CH2:17][CH2:18][CH2:19][O:20][CH:15]3[C:14]3[C:13]([N+:21]([O-])=O)=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CCO>[CH:1]1([CH:7]2[CH:16]3[CH2:17][CH2:18][CH2:19][O:20][CH:15]3[C:14]3[C:13]([NH2:21])=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 78145418HCID 78145418, compound

Product 1

HCID 126634529HCID 126634529, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  1. customwas purged with nitrogen
  2. customthe reaction mixture was purged with nitrogen
  3. filtrationThe suspension was filtered over celite
  4. customthe solvent removed under reduced pressure
  5. customThe remaining residue was purified by Combiflash chromatography (SiO2, c-Hexane/AcOEt)

Sources & evidence

ORD record
ord-ec1d7e4477314b5fb27c2850457e73f8
Source dataset
uspto-grants-2015_11
Patent number
US09193738B2

Reaction notes

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