Trifluoroacetic acid → (R)-methyl-[1-(4-nitrophenyl)pyrrolidin-3-yl]amine

HRID 1354671Notes

Reaction equation

HRID 1354671 reaction equation
[CH3:1][N:2]([C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:11]1)C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C@@H:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67148139tert-Butyl (R)-methyl-[1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate

Product 1

HCID 67147986(R)-methyl-[1-(4-nitrophenyl)pyrrolidin-3-yl]amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (R)-methyl-[1-(4-nitrophenyl)pyrrolidin-3-yl]-carbamate (0.7 g) in dichloromethane (5 ml) was treated with trifluoroacetic acid (3 ml) for 1 hour. The reaction solution was concentrated and the residue was taken up in dichloromethane. After washing with sodium carbonate solution, the organic phase was dried over magnesium sulfate and concentrated. This resulted in the product with the molecular weight of 221.26 (C11H15N3O2); MS (ESI): 222 (M+H+).

Workup

  1. concentrationThe reaction solution was concentrated
  2. washAfter washing with sodium carbonate solution
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThis resulted in the product with the molecular weight of 221.26 (C11H15N3O2)

Sources & evidence

ORD record
ord-41a16afa3abf4b61b8c86a94252861c5
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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