Potassium Carbonate → (R)-1-(5-Amino-2-chloro-4-nitro-phenyl)-2-hydroxymethyl-pyrrolidine

HRID 1258666Notes

Reaction equation

HRID 1258666 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.C(=O)([O-])[O-].[K+].[K+].[Cl:14][C:15]1[C:20](Cl)=[CH:19][C:18]([NH2:22])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.C(O)(C(F)(F)F)=O.O>CN(C=O)C.O>[NH2:22][C:18]1[C:17]([N+:23]([O-:25])=[O:24])=[CH:16][C:15]([Cl:14])=[C:20]([N:4]2[CH2:5][CH2:6][CH2:7][C@@H:3]2[CH2:2][OH:1])[CH:19]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 811494,5-Dichloro-2-nitroanilineHCID 2724541Prolinol, (R)-HCID 22392675Trifluoroacetic acid water

Product 1

HCID 67957823(R)-1-(5-Amino-2-chloro-4-nitro-phenyl)-2-hydroxymethyl-pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(R)-2-Hydroxymethyl-pyrrolidine (202 mg, 2.0 mmol) followed by potassium carbonate (304 mg, 2.2 mmol) were added to a mixture of 4,5-dichloro-2-nitro-phenylamine (414 mg, 2.0 mmol) in DMF (10 mL) and stirred at rt overnight. The reaction mixture was diluted with water, acidified with TFA:H2O 1:1 and filtered. The filtercake was washed with DMF:H2O 1:1 and dried to give the sub-title compound.

Workup

  1. filtrationfiltered
  2. washThe filtercake was washed with DMF:H2O 1:1
  3. customdried

Sources & evidence

ORD record
ord-5c4a171d562141d3b810991ad0bbb110
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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