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

HRID 594951Notes

Reaction equation

HRID 594951 reaction equation
[CH:1]12[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]=[C:2]2[C:16]([O:18][CH3:19])=[O:17]>CO>[CH:1]12[N:8]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH:2]2[C:16]([O:18][CH3:19])=[O:17]

Participants

3

Reactant 1

HCID 10221000HCID 10221000, compound

Product 1

HCID 580172018-(1,1-Dimethylethyl) 2-methyl 8-azabicyclo[3.2.1]octane-2,8-dicarboxylateYield 94.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-tert-butyl 2-methyl 8-azabicyclo[3.2.1]oct-2-ene-2,8-dicarboxylate (880 mg, 3.29 mmol) was dissolved in methanol (15 ml). The reaction flask was flushed with argon and 5% palladium hydroxide on carbon (88 mg) was added. The flask was degassed under vacuum. Hydrogen gas is then added via balloon. The reaction is stirred under hydrogen atmosphere for 16 hours. The reaction was then filtered through celite, and concentrated to give the titled compound (840 mg).

Workup

  1. customThe reaction flask was flushed with argon and 5% palladium hydroxide on carbon (88 mg)
  2. additionwas added
  3. customThe flask was degassed under vacuum
  4. additionHydrogen gas is then added via balloon
  5. filtrationThe reaction was then filtered through celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a411bbda7f594b8c856ddc1845e411ac
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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