Potassium Carbonate → 1-Benzyl 3-methyl (S)-pyrazolidine-1,3-dicarboxylate

HRID 1396836Notes

Reaction equation

HRID 1396836 reaction equation
I[CH2:2][CH2:3][C@H:4]([NH:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+]>CC#N>[N:10]1([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:2][CH2:3][C@@H:4]([C:5]([O:7][CH3:8])=[O:6])[NH:9]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68287973phenylmethyl 2-{(1S)-3-iodo-1-[(methyloxy)carbonyl]propyl}hydrazinecarboxylate

Product 1

HCID 594155711-Benzyl 3-methyl (S)-pyrazolidine-1,3-dicarboxylateYield 121.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of phenylmethyl 2-{(1S)-3-iodo-1-[(methyloxy)carbonyl]propyl}hydrazinecarboxylate (3.38 g, 8.6 mmol) in CH3CN (500 mL) was added K2CO3 (2.38 g, 17.2 mmol), and the mixture was stirred overnight at rt. LC-MS showed that all starting material was consumed. The mixture was filtered, and the filtrate was concentrated to provide the crude 3-methyl 1-(phenylmethyl) (3S)-1,3-pyrazolidinedicarboxylate as an oil (2.77 g, 100%) without further purification.

Workup

  1. customwas consumed
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d7752be1de2848aea08afee21620b513
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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