HCID 86704450, compound → HCID 86704452, compound

HRID 1754396Notes

Reaction equation

HRID 1754396 reaction equation
[N:1]([C:4]1[CH:12]=[C:11]2[N:7]([C:8]([CH3:14])([CH3:13])[CH2:9][CH2:10]2)[C:6](=[O:15])[CH:5]=1)=[N+]=[N-]>CCO.[Pd]>[NH2:1][CH:4]1[CH2:12][CH:11]2[N:7]([C:8]([CH3:13])([CH3:14])[CH2:9][CH2:10]2)[C:6](=[O:15])[CH2:5]1

Participants

4

Reactant 1

HCID 86704450HCID 86704450, compound

Product 1

HCID 86704452HCID 86704452, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Azido-3,3-dimethylindolizin-5(1H)-one (0.3 g, 1.5 mmol) is dissolved in EtOH (20 ml). The clear solution is transferred to a Parr hydrogenation flask and placed under nitrogen. 10% Pd—C (0.25 g) was added to the Parr flask under nitrogen. The mixture was then transferred to a Pan hydrogenation apparatus, evacuated and filled with hydrogen (×3). The mixture was hydrogenated at 30 psi (optionally topping-up hydrogen) until LC/MS and TLC indicated complete reaction to the amine. After complete reaction, the mixture was placed under nitrogen and filtered through a small pad of Celite. The filter cake was washed with MeOH (×3) and the filtrate was concentrated under vacuum to leave the 7-amino-hexahydro-3,3-dimethylindolizin-5-(1H)-one in 89% yield (0.25 g).

Workup

  1. customevacuated
  2. additionfilled with hydrogen (×3)
  3. customreaction to the amine
  4. customAfter complete reaction
  5. filtrationfiltered through a small pad of Celite
  6. washThe filter cake was washed with MeOH (×3)
  7. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-68019c724fae4c778928b9efface4d5a
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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