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

HRID 384274Notes

Reaction equation

HRID 384274 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([OH:9])=O.[N+:10]([C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16])([O-:12])=[O:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCOC(C)=O>CN(C=O)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([NH:16][C:15]1[CH:17]=[CH:18][CH:19]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=1)=[O:9]

Participants

6

Reactant 4

HCID 74233-NitroanilineHCID 8857Ethyl AcetateHCID 643474N-Methyl-L-prolineHCID 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 20 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-7760a9c4e9614551838fd69645675a0c
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Reaction notes

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