1-(3-Aminophenyl)pyrrolidin-2-one → HCID 178454279, compound

HRID 42261Notes

Reaction equation

HRID 42261 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH3:14][C:15]([CH3:31])([O:17][C:18](=[O:30])[NH:19][C:20](=S)[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:16]>C(Cl)Cl>[C:24]([O:23][C:22]([NH:21]/[C:20](=[N:19]/[C:18](=[O:30])[O:17][C:15]([CH3:31])([CH3:16])[CH3:14])/[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:3]=1)=[O:28])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 6839561-(3-Aminophenyl)pyrrolidin-2-oneHCID 5193990N,N'-Di-Boc-thiourea

Product 1

HCID 178454279HCID 178454279, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 500 mL round bottom flask was charged 1-(3-aminophenyl)pyrrolidin-2-one (5 g, 28.4 mmol), 2,2,10,10-tetramethyl-6-thioxo-3,9-dioxa-5,7-diazaundecane-4,8-dione (9.80 g, 35.5 mmol), polystyrene-carbodiimide (Argonaut P/N 800371, 1.42 mmole/g, 30.0 g, 42.6 mmol) and CH2Cl2 (300 mL). The resulting suspension was stirred at room temperature for 14 hours. The reaction was filtered and the collected solid was washed with 2×30 mL CH2Cl2. The filtrate was concentrated. The concentrate was purified by flash chromatography on a 140 g silica gel plug eluting with CH2Cl2 then 1:1 ethyl acetate/hexanes to provide the title compound. MS (ESI+) m/e 419.1 (M+H)+.

Workup

  1. filtrationThe reaction was filtered
  2. washthe collected solid was washed with 2×30 mL CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customThe concentrate was purified by flash chromatography on a 140 g silica gel plug
  5. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-2510f83b7b6b426e8032cbb3a37550e0
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Reaction notes

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