HCID 54105171, compound → HCID 53986216, compound

HRID 843720Notes

Reaction equation

HRID 843720 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:7]([NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8])[CH3:2]>C(O)(=O)C.O=[Pt]=O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]1)=[O:8])[CH3:2]

Participants

4

Reactant 1

HCID 54105171HCID 54105171, compound

Product 1

HCID 53986216HCID 53986216, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N-(3-pyridyl)-3(R)-(tert-butoxycarbonylamino)succinamic acid ethyl ester (0.62 g) and PtO2 (0.06 g) in acetic acid (12 ml) was hydrogenated. at atmospheric pressure for 6 hours. After the catalyst was removed by filtration, the filtrate was concentrated in vacuo. The residue was dissolved in water. The solution was adjusted to pH 10 with saturated aqueous potassium carbonate solution, and extracted with ethyl acetate. The extract was washed with water and brine, and dried over MgSO4, and evaporated in vacuo to give N-(3-piperidyl)-3(R)-(tert-butoxycarbonylamino)succinamic acid ethyl ester (0.51 g) as an oil.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6e14fb2e45ac4e6dbd9943ada48016fa
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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