Ethylene Glycol → Benzyl 4-(1,3-dioxolan-2-yl)piperidine-1-carboxylate

HRID 220831Notes

Reaction equation

HRID 220831 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH:32]=O)[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH:32]2[O:4][CH2:1][CH2:2][O:3]2)[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 57555344Benzyl 4-(1,3-dioxolan-2-yl)piperidine-1-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethylene glycol (5 ml) and a catalytic amount of p-toluenesulfonic acid were added to 4-formyl-piperidine-1-carboxylic acid benzyl ester from Example E33.2 (5.6 g, 22.6 mmol) in toluene (100 ml) and the mixture was heated at reflux under Dean and Stark conditions for 2.5 h. Solvents were removed in vacuo and the residue was redissolved in EtOAc, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 50% EtOAc:50% pet. ether) to yield the title compound (5.14 g, 78%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under Dean and Stark conditions for 2.5 h
  3. customSolvents were removed in vacuo
  4. dissolutionthe residue was redissolved in EtOAc
  5. washwashed with saturated NaHCO3
  6. dry with materialbrine, dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluant; 50% EtOAc:50% pet. ether)

Sources & evidence

ORD record
ord-3620df83035048c7be749a126f9619b9
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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