Acetic Acid → Bis(1,1-dimethylethyl) 2-methyl-1,5-pyrazolidinedicarboxylate

HRID 1396884Notes

Reaction equation

HRID 1396884 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C=O.[C:22](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH3:22][N:9]1[CH2:10][CH2:11][CH:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68287714Di-tert-butyl pyrazolidine-1,5-dicarboxylate

Product 1

HCID 68287657Bis(1,1-dimethylethyl) 2-methyl-1,5-pyrazolidinedicarboxylateYield 54.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of di-tert-butylpyrazolidine-1,5-dicarboxylate (7 g, 25.7 mmol) dissolved in 1,2-dichloroethane (DCE) (80 mL) were added HCHO (2.224 g, 69.4 mmol), sodium triacetoxyborohydride (14.71 g, 69.4 mmol), and acetic acid (8 mL). The reaction was stirred at rt for appropriate time. The solvent was then removed and the residue was diluted with DCM and saturated NaHCO3 (150 mL). The aqueous layer was extracted with DCM. The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by silica gel column chromatography to afford 4 g (13.97 mmol, 54.3% yield) of bis(1,1-dimethylethyl) 2-methyl-1,5-pyrazolidinedicarboxylate as a pale yellow oil. LC-MS (ES) m/e 287.1 (M+H)+.

Workup

  1. customThe solvent was then removed
  2. additionthe residue was diluted with DCM and saturated NaHCO3 (150 mL)
  3. extractionThe aqueous layer was extracted with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a5c9b7e2e01541dabbba6f310d321f6d
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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