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

HRID 2426616Notes

Reaction equation

HRID 2426616 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-a1cad2989745491893a193ee15e3f6dd
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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