Pyridine → 1-tert-Butyl 4-(pentafluorophenyl) piperidine-1,4-dicarboxylate

HRID 1612375Notes

Reaction equation

HRID 1612375 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.FC(F)(F)C(O[C:28]1[C:33]([F:34])=[C:32]([F:35])[C:31]([F:36])=[C:30]([F:37])[C:29]=1[F:38])=O>C1COCC1.CC(=O)OCC>[CH3:3][C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][C:28]2[C:29]([F:38])=[C:30]([F:37])[C:31]([F:36])=[C:32]([F:35])[C:33]=2[F:34])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 4327891Pentafluorophenyl Trifluoroacetate

Product 1

HCID 117497801-tert-Butyl 4-(pentafluorophenyl) piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 g (436 mmol) of piperidine-1,4-dicarboxylic acid 1-tert butyl ester were dissolved in 1.3 l of anhydrous THF, 39 ml of anhydrous pyridine were added and 86 ml (500 mmol) of pentafluorophenyl trifluoroacetate were added dropwise with stirring and with ice-cooling in the course of 30 minutes, and the mixture was allowed to stand at room temperature for 3 h. The solvent was then stripped off in vacuo and the residue was taken up in about 2 l of EA, extracted twice each with 0.5 N HCl, saturated NaHCO3 solution and saturated NaCl solution, and the organic phase was dried over Na2SO4. After evaporating off the solvent in vacuo, an oil remained which crystallized after addition of heptane. Yield 151.5 g (88%), colorless crystals. M.p. 87–88° C. (heptane).

Workup

  1. temperaturecooling in the course of 30 minutes
  2. extractionextracted twice each with 0.5 N HCl, saturated NaHCO3 solution and saturated NaCl solution
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customAfter evaporating off the solvent in vacuo
  5. customcrystallized
  6. additionafter addition of heptane

Sources & evidence

ORD record
ord-8d673bfe829149ceac13f0140987bb34
Source dataset
uspto-grants-2006_01
Patent number
US06992187B2

Reaction notes

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