3-Nitroaniline → (S)-1-methyl-N-(3-nitrophenyl)pyrrolidine-2-carboxamide

HRID 533478Notes

Reaction equation

HRID 533478 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].CN(C(ON1N=N[C:21]2[CH:22]=[CH:23][CH:24]=[N:25][C:20]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[CH2:36][O:37]C(C)=O>CN(C=O)C>[CH3:20][N:25]1[CH2:24][CH2:23][CH2:22][C@H:21]1[C:36]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:37]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 8857Ethyl AcetateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 58098896(S)-1-methyl-N-(3-nitrophenyl)pyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of(S)-1-methylpyrrolidine-2-carboxylic acid (258 mg, 2 mmol) in DMF (4 mL) was added 3-nitroaniline (276 mg, 2 mmol) and HATU (760 mg). After stirring for h, it was added with EtOAc, washed with Sat. NaHCO3, brine, dried and concentrated to give (S)-1-methyl-N-(3-nitrophenyl)pyrrolidine-2-carboxamide.

Workup

  1. washwashed with Sat. NaHCO3, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-463628d652844cc984878f747192de9d
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

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