Acetic Acid → cis-1,3,4,4a,9,9a-Hexahydro-indeno[2,1-b]pyridin-2-one

HRID 455348Notes

Reaction equation

HRID 455348 reaction equation
[NH:1]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH2:14][C:2]1=2.C(O)(=O)C>[Pd].CO>[NH:1]1[C:6](=[O:7])[CH2:5][CH2:4][C@@H:3]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH2:14][C@H:2]12

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 581238621,3,4,9-Tetrahydro-indeno[2,1-b]pyridin-2-one

Product 1

HCID 58124040cis-1,3,4,4a,9,9a-Hexahydro-indeno[2,1-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,3,4,9-tetrahydro-indeno[2,1-b]pyridin-2-one (1.10 g), 10% palladium on carbon (0.15 g), acetic acid (0.75 mL), and methanol (20 mL) is shaken under hydrogen atmosphere (3 bar) at room temperature for 6 h. The catalyst is then separated by filtration and the filtrate is concentrated. The residue is triturated with tert-butyl methyl ether and dried to give the title compound as a colorless solid. Yield: 0.99 g (89% of theory); LC (method 1): tR=2.53 min; Mass spectrum (ESI+): m/z=188 [M+H]+.

Workup

  1. customThe catalyst is then separated by filtration
  2. concentrationthe filtrate is concentrated
  3. customThe residue is triturated with tert-butyl methyl ether
  4. customdried

Sources & evidence

ORD record
ord-688225bc275548d489f6efeb668da2ad
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Reaction notes

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