Triethylamine → 1-Benzyl 3-tert-butyl 1,3-pyrazolidinedicarboxylate

HRID 1396846Notes

Reaction equation

HRID 1396846 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[NH:2]1.C(N(CC)CC)C.[CH2:20]([O:27][C:28](ON1C(=O)CCC1=O)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[N:1]1([C:28]([O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:29])[CH2:5][CH2:4][CH:3]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[NH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 57015512tert-Butyl pyrazolidine-3-carboxylate

Product 1

HCID 133415401-Benzyl 3-tert-butyl 1,3-pyrazolidinedicarboxylateYield 110.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C., to a 50 mL round bottomed flask charged with 1,1-dimethylethyl 3-pyrazolidinecarboxylate (0.054 g, 0.259 mmol) and stirrer in dichloromethane (DCM) (3 mL), was added triethylamine (0.079 mL, 0.569 mmol). After a couple of minutes, N-(benzyloxycarbonyloxy)succinimide (CBz-OSu) (0.064 g, 0.259 mmol) in dichloromethane (DCM) (1.5 mL) was added dropwise. The reaction mixture stirred at 0° C. for one hour, then warmed to r.t. After 2 hr at r.t., the solvent was evaporated and the residue was dissolved in EtOAc (30 mL), washed with water (15 mL×2), sat. NaHCO3 (15 ml), brine (15 mL), dried over Na2SO4 and concentrated to afford the crude product as a colorless gum (88 mg).

Workup

  1. waitAfter a couple of minutes
  2. temperaturewarmed to r.t
  3. waitAfter 2 hr at r.t.
  4. customthe solvent was evaporated
  5. dissolutionthe residue was dissolved in EtOAc (30 mL)
  6. washwashed with water (15 mL×2), sat. NaHCO3 (15 ml), brine (15 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dd9ee9b5f3b3499ab6e2c46b0b678b09
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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