HCID 19738093, compound → HCID 19738102, compound

HRID 2255421Notes

Reaction equation

HRID 2255421 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:12]=[C:13]([CH:14]([CH3:16])[CH3:15])[CH:8]([CH:9]([CH3:17])[NH:10]2)[CH2:7]1)=[O:5])[CH3:2].[H][H]>[Pt]=O.C(O)(=O)C>[CH3:17][CH:9]1[CH:8]2[CH:13]([CH:14]([CH3:15])[CH3:16])[CH2:12][CH:11]([CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7]2)[NH:10]1

Participants

5

Reactant 2

HCID 19738093HCID 19738093, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19738102HCID 19738102, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl-3-methyl-8-isopropyl-2-azabicyclo[2.2.2]oct-7-ene-6-carboxylate (21.4 g, 78 mmol), acetic acid (200 mL) and platinum oxide (2.1 g) was placed on a Parr hydrogenator at 44 psi of hydrogen pressure for 41/4 hours. The catalyst was removed by filtration and the solvent was removed in vacuo. The residue was dissolved in water, neutralized with NH4OH to a pH of 10 and the mixture was extracted with CH2Cl2 (3×50 mL). The organic layers were combined, washed with brine and dried over MgSO4. The solvent was removed in vacuo to afford 18.1 g (97%) of ethyl 3-methyl-8-isopropyl-2-azabicyclo-[2.2.2]octane-6-carboxylate. The product was dissolved in ethanol and treated with 6.9N ethanolic HCl to afford 10.2 g of the hydrochloride salt as a white solid, m.p. 157.5°-158.5° C.

Workup

  1. custom4 hours
  2. customThe catalyst was removed by filtration
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in water
  5. extractionthe mixture was extracted with CH2Cl2 (3×50 mL)
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-14a7d0972af84c21aa084b14e04c1a31
Source dataset
uspto-grants-1993_08
Patent number
US05240935

Reaction notes

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