4-(Trifluoromethyl)aniline → Methyl 3-(4-trifluoromethylanilino)pentanoylcarbamate

HRID 898822Notes

Reaction equation

HRID 898822 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[C:12]([NH:18][C:19](=[O:22])[O:20][CH3:21])(=[O:17])[CH:13]=[CH:14][CH2:15][CH3:16]>C1(C)C=CC=CC=1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][CH:14]([CH2:15][CH3:16])[CH2:13][C:12]([NH:18][C:19](=[O:22])[O:20][CH3:21])=[O:17])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 73030491Methyl 2-pentenoylcarbamate

Product 1

HCID 20621451Methyl 3-(4-trifluoromethylanilino)pentanoylcarbamateYield 99.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-trifluoromethylaniline (121 mg, 0.75 mmol) and methyl 2-pentenoylcarbamate (79 mg, 0.5 mmol) in toluene (2 ml) in a stream of nitrogen was added Pd((S)-dm-binap)(H2O)2(OTf)2 (14.7 mg, 0.0125 mmol) and the resulting mixture was stirred at 50° C. for 5 hours. After completion of the reaction, the reaction mixture was concentrated and the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1) to give the objective compound methyl 3-(4-trifluoromethylanilino)pentanoylcarbamate (159 mg, 50% yield). Enantiomeric excess ratio of this product was determined by a liquid chromatography using a column for separation of optical isomers (column: OJ-R) to be 61% e.e. (R form).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-db2acc4ed15c40708373ee6d0c53aaad
Source dataset
uspto-grants-2008_04
Patent number
US07351849B2

Reaction notes

Loading…