Hydrochloric Acid → HCID 17981664, compound

HRID 2252039Notes

Reaction equation

HRID 2252039 reaction equation
Cl.[NH2:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=O.[CH2:9]([O:11][C:12](=[O:22])[CH2:13][C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:10].CC[O-].[Na+].Cl>O.C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:9]([O:11][C:12]([C:13]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:2][N:3]2[CH2:7][CH2:6][CH2:5][C:4]=12)=[O:22])[CH3:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7170Ethyl benzoylacetateHCID 2723922Sodium ethoxideHCID 219928451-Aminopyrrolidin-2-one hydrochloride

Product 1

HCID 17981664HCID 17981664, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-amino-pyrrolidine-2-one hydrochloride (3.8 g, 27.8 mmol) (WO 02/094833) add ethylbenzoylacetate (4.3 mL, 25 mmol) followed by pyridine (10 mL) at room temperature under nitrogen. Stir the mixture at room temperature for 20 hours and then, dilute with water (50 mL) and extract with toluene (2×50 mL). Dry the combined organic layers (MgSO4) and concentrate in vacuo to give a brown oil, 6.23 g, 82% yield, and treat with NaOEt (freshly prepared, 3.1 g, 45.4 mmol, 2 equiv) in toluene at 120° C. for 8 hours. Cool the mixture to room temperature and add water (100 mL) and concentrated HCl until a pH of 4 is reached. Extract the mixture with EtOAc (3×200 mL) and dry (MgSO4) the combined organic layers and concentrate in vacuo. Purify the residue in a biotage system (eluent:CH2Cl2/MeOH 40:1) to obtain a yellow solid, 1.8 g, 36% yield. MS(ES+): m/z=257.1 (M+H)+

Workup

  1. extractionextract with toluene (2×50 mL)
  2. dry with materialDry the combined organic layers (MgSO4)
  3. concentrationconcentrate in vacuo
  4. customto give a brown oil, 6.23 g, 82% yield
  5. customfreshly prepared
  6. temperatureCool the mixture to room temperature
  7. extractionExtract the mixture with EtOAc (3×200 mL)
  8. dry with materialdry (MgSO4) the combined organic layers
  9. concentrationconcentrate in vacuo
  10. customPurify the residue in a biotage system (eluent:CH2Cl2/MeOH 40:1)
  11. customto obtain a yellow solid, 1.8 g, 36% yield

Sources & evidence

ORD record
ord-3d3f42fc2d994b119a194b32ba1c073a
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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