Pyridine → 2,3-Bis(1,1-dimethylethyl) 1-(2-propen-1-yl) 1,2,3-pyrazolidinetricarboxylate

HRID 1396913Notes

Reaction equation

HRID 1396913 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3].[N:8]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:10][NH:9]1.N1C=CC=CC=1>O1CCCC1>[N:9]1([C:2]([O:4][CH2:5][CH:6]=[CH2:7])=[O:3])[CH2:10][CH2:11][CH:12]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[N:8]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 18052Allyl chloroformateHCID 68287714Di-tert-butyl pyrazolidine-1,5-dicarboxylate

Product 1

HCID 867063572,3-Bis(1,1-dimethylethyl) 1-(2-propen-1-yl) 1,2,3-pyrazolidinetricarboxylateYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Allyl chloroformate (0.488 ml, 4.59 mmol) was added dropwise to the solution of di-tert-butyl pyrazolidine-1,5-dicarboxylate (1 g, 3.67 mmol) and pyridine (0.371 ml, 4.59 mmol) in tetrahydrofuran (THF) (1.79 ml) at 0° C. The resulting solution was allowed to warm up to ambient temperature and stirred for 30 min. The reaction was filtered, and to the filtrate was added EtOAc. The solution was washed with brine. The organic layers were separated and dried over anhydrous Na2SO4. The crude product was purified by RP-HPLC to give 2,3-bis(1,1-dimethylethyl) 1-(2-propen-1-yl) 1,2,3-pyrazolidinetricarboxylate (749 mg, 2.101 mmol, 57% yield). MS (ES+) m/z 357.3 (MH+).

Workup

  1. filtrationThe reaction was filtered
  2. additionto the filtrate was added EtOAc
  3. washThe solution was washed with brine
  4. customThe organic layers were separated
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-cecc4d4c1ee84a3cb657f2259970bd9c
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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