Hydrochloric Acid → HCID 20110077, compound

HRID 1500918Notes

Reaction equation

HRID 1500918 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][CH:10](C(N)=O)[CH2:9]2)=[CH:5][CH:4]=1.C(OI(OC(=O)C)C1C=CC=CC=1)(=O)C.Cl.CC#[N:37]>O>[NH2:37][CH:10]1[CH2:9][N:8]([CH2:7][C:6]2[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:12](=[O:13])[CH2:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 76724Iodobenzene diacetateHCID 82131111HCID 82131111, compound

Product 1

HCID 20110077HCID 20110077, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 1-(4-methoxy-benzyl)-5-oxo-pyrrolidine-3-carboxylic acid amide (50.0 g, 201 mmol) in 560 mL of CH3CN and 560 mL of H2O was added bis(acetyloxy)(phenyl)-λ3-iodane (84.0 g, 261 mmol). The color of the mixture turned to light red. After being stirred at room temperature overnight, the reaction mixture was diluted with 1000 mL of H2O and acidified to pH 2 with concentrated HCl, then extracted with DCM (300 mL×3). The aqueous layer was then basified to pH 10 with 1 N aqueous solution of KOH and then extracted with DCM (400 mL×3). The combined organic layers were dried over Na2SO4 and then concentrated in vacuo to afford 4-amino-1-(4-methoxybenzyl)pyrrolidin-2-one as light yellow oil (28.0 g, yield: 63.2%), which solidified after being cooled down to room temperature and was used without further purification.

Workup

  1. extractionextracted with DCM (300 mL×3)
  2. extractionextracted with DCM (400 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c00f03dff3104abb87b9859f03d20398
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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