Diethyl Ether → 3-Amino-1-methyl-3-prop-2-ynyl-pyrrolidin-2-one

HRID 2207686Notes

Reaction equation

HRID 2207686 reaction equation
O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=[N:28][C:29]1([CH2:36][C:37]#[CH:38])[CH2:33][CH2:32][N:31]([CH3:34])[C:30]1=[O:35])(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>C1COCC1>[NH2:28][C:29]1([CH2:36][C:37]#[CH:38])[CH2:33][CH2:32][N:31]([CH3:34])[C:30]1=[O:35]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 896495353-(Benzhydrylidene-amino)-1-methyl-3-prop-2-ynyl-pyrrolidin-2-one

Product 1

HCID 896492053-Amino-1-methyl-3-prop-2-ynyl-pyrrolidin-2-oneYield 107.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Citric acid monohydrate (10.39 g, 49.46 mmol) was added to a solution of 3-(benzhydrylidene-amino)-1-methyl-3-prop-2-ynyl-pyrrolidin-2-one (6.26 g, 19.79 mmol) (which may be prepared as described in Description 2) in THF (150 mL) and the reaction was stirred at room temperature for 18 hours. A colourless solid precipitated out. The solvent was evaporated to give a gummy white solid. This was trituated with Et2O and the solid was washed with further Et2O. The solid was suspended in water/MeOH and purified by SCX (70 g Silca), eluting with water/MeOH, MeOH and finally 0.5M NH3 in MeOH. Fractions containing product were evaporated to afford 3-amino-1-methyl-3-prop-2-ynyl-pyrrolidin-2-one (3.23 g, 21.223 mmol) as a pale yellow oil;

Workup

  1. customA colourless solid precipitated out
  2. customThe solvent was evaporated
  3. customto give a gummy white solid
  4. washthe solid was washed with further Et2O
  5. custompurified by SCX (70 g Silca)
  6. washeluting with water/MeOH, MeOH and finally 0.5M NH3 in MeOH
  7. additionFractions containing product
  8. customwere evaporated

Sources & evidence

ORD record
ord-af6e4cd407ed439da0cdd6713605b12e
Source dataset
uspto-grants-2016_06
Patent number
US09376445B2

Reaction notes

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