HCID 10221000, compound → 8-(1,1-Dimethylethyl) 2-methyl 8-azabicyclo[3.2.1]octane-2,8-dicarboxylate

HRID 1895039Notes

Reaction equation

HRID 1895039 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:9]([CH2:10][CH:11]=1)[CH2:8][CH2:7]2)=[O:4]>C(O)C.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:11][CH2:10][CH:9]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]1[CH2:7][CH2:8]2)=[O:4]

Participants

4

Reactant 1

HCID 10221000HCID 10221000, compound

Product 1

HCID 580172018-(1,1-Dimethylethyl) 2-methyl 8-azabicyclo[3.2.1]octane-2,8-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8-Azabicyclo[3.2.1]oct-2-ene-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester from Step 4 (5.9 g, 22 mmol) was dissolved in ethanol (100 mL), to which palladium (10% on charcoal, 0.59 g) was added. The resulting mixture was shaken under an atmosphere of hydrogen (50 psi) for 2 hours at room temperature, and was then filtered through a bed of Celite, which was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by flash chromatography (silica gel, ethyl acetate/hexane) to provide 8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester as a mixture of endo and exo isomers as a colorless oil (5.8 g, 97% yield).

Workup

  1. additionwas added
  2. filtrationwas then filtered through a bed of Celite, which
  3. washwas washed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by flash chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3080672bb5964e38b3a7a20852eeaa50
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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