Benzyl 1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-ylcarbamate → 4-Amino-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one

HRID 1993380Notes

Reaction equation

HRID 1993380 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([NH:16]C(=O)OCC3C=CC=CC=3)[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]>CCOC(C)=O.[Pd]>[NH2:16][CH:12]1[CH2:11][N:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)[C:14](=[O:15])[CH2:13]1

Participants

4

Reactant 1

HCID 57445404Benzyl 1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-ylcarbamate

Product 1

HCID 435211184-Amino-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a round-bottomed flask containing a mixture of benzyl 1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-ylcarbamate (Step 1, 1.5 g, 4.2 mmol) and 200 mg of Pd/C in 100 mL of EtOAc was applied with a H2 balloon. The reaction was stirred at RT for 8 h, and filtered with the aid of Celite®. The filtrate was concentrated in vacuo to give the title compound as a white solid. MS (ESI pos. ion) m/z: 225.3 (M+H). Calc'd Exact Mass for C11H13FN2O2: 224.23.

Workup

  1. additionIn a round-bottomed flask containing
  2. filtrationfiltered with the aid of Celite®
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-821287ef185c4903a12c798a1e0fc10f
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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