Trifluoroacetic acid → (1-Benzyl-2,5-dihydro-1H-pyrrol-3-yl)-ethanone

HRID 906875Notes

Reaction equation

HRID 906875 reaction equation
CO[CH2:3][N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][Si](C)(C)C.[CH3:17][C:18](=[O:21])[C:19]#[CH:20].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:10]([N:4]1[CH2:3][CH:20]=[C:19]([C:18](=[O:21])[CH3:17])[CH2:5]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15018Butyn-2-oneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

Product 1

HCID 57576371(1-Benzyl-2,5-dihydro-1H-pyrrol-3-yl)-ethanoneYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (9.76 g, 0.041 mol) in CH2Cl2 (40 mL) at 0° C., was added dropwise over a 5 minutes period but-3-yn-2-one (2.0 g, 0.029 mol) followed by trifluoroacetic acid (0.22 mL, 0.003 mol) (very exothermic reaction). The ice bath was removed after 30 minutes, and the solution was stirred at 25° C. for an additional 2 h. It was then concentrated and purification by flash chromatography (SiO2, EtOAc/Heptane 1:1) afforded 2.90 g (49%) of the title compound as a yellow oil. ES-MS m/e: 202.2 (M+H+).

Workup

  1. customvery exothermic reaction)
  2. customThe ice bath was removed after 30 minutes
  3. concentrationIt was then concentrated
  4. custompurification by flash chromatography (SiO2, EtOAc/Heptane 1:1)

Sources & evidence

ORD record
ord-05508a65e39d4cd8b030f813b04574f2
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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