Trifluoroacetic acid → 1-Benzyl-3-(3,5-dichloro-2-fluoro-phenyl)-3-(trifluoromethyl)pyrrolidine

HRID 2206928Notes

Reaction equation

HRID 2206928 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]([C:11]([F:14])([F:13])[F:12])=[CH2:10])[C:3]=1[F:15].CO[CH2:18][N:19]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:20][Si](C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:25]([N:19]1[CH2:20][CH2:10][C:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=2[F:15])([C:11]([F:14])([F:13])[F:12])[CH2:18]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 871590141,5-Dichloro-2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 871585151-Benzyl-3-(3,5-dichloro-2-fluoro-phenyl)-3-(trifluoromethyl)pyrrolidineYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,5-dichloro-2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)benzene (6.2 g) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (4.7 g) were dissolved in dichloromethane (100 ml) and slowly added dropwise with a dichloromethane solution (8 ml) of anhydrous trifluoroacetic acid (0.15 ml) under ice cooling. Upon the completion of the dropwise addition, the reaction temperature was raised to the room temperature and stirred overnight. The reaction solution was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain 1-benzyl-3-(3,5-dichloro-2-fluorophenyl)-3-(trifluoromethyl)pyrrolidine (3.7 g).

Workup

  1. additionUpon the completion of the dropwise addition
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a76b0ad8d147499f92ff92ea5a3a3781
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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