HCID 86695586, compound → HCID 86695587, compound

HRID 1465721Notes

Reaction equation

HRID 1465721 reaction equation
[C@H:1]12[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]=[C:2]2[C:16]([O:18][CH3:19])=[O:17]>C(O)C.[OH-].[Pd+2].[OH-]>[C@H:1]12[N:8]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C@H:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH:2]2[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 1

HCID 86695586HCID 86695586, compound

Product 1

HCID 86695587HCID 86695587, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(1S,5R)-8-tert-butyl 2-methyl 8-azabicyclo[3.2.1]oct-2-ene-2,8-dicarboxylate (5.45 g) was dissolved in ethanol (200 mL), Palladium hydroxide (20% wt, 2.73 g) was added. After vacuum degassed, the reaction mixture was hydrogenated under hydrogen balloon overnight. After filter through a pad of celite, washed with ethanol, the filtrate was concentrated to give 5.49 g of crude product. The crude was brought to next step without further purification.

Workup

  1. customAfter vacuum degassed
  2. customballoon overnight
  3. filtrationAfter filter through a pad of celite
  4. washwashed with ethanol
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-645fd826917b48078792c727179da72f
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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