Trifluoroacetic acid → 2-(2-(4-Ethoxycarbonylphenyl)ethynyl)pyrrolidine

HRID 354276Notes

Reaction equation

HRID 354276 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]#[C:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:24]([O:23][C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:14]#[C:13][CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][CH:17]=1)=[O:22])[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 235119181-(Tert-butoxycarbonyl)-2-[2-(4-ethoxycarbonylphenyl)ethynyl]pyrrolidine

Product 1

HCID 235119142-(2-(4-Ethoxycarbonylphenyl)ethynyl)pyrrolidineYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(tert-butoxycarbonyl)-2-[2-(4-ethoxycarbonylphenyl)ethynyl]pyrrolidine (2.75 g, 8 mmol) in CH2Cl2 (5 ml) was added TFA (5 mL), and the resulting mixture was stirred overnight. The mixture was concentrated in vacuo and made basic with sat. NaHCO3 and extracted with CHCl3. The extract was washed with brine, dried over MgSO4, evaporated to give 1.95 g (q.y.) 2-[2-(4-ethoxycarbonylphenyl)ethynyl]pyrrolidine as a light yellow oil. 1H-NMR (CDCl3) δ1.38 (3 H, t, J=6.8 Hz), 1.82-2.16 (4 H, m), 3.01-3.48 (2 H, m), 4.00-4.11 (1 H, m), 4.37 (2H, q, J=6.8 Hz), 4.54-4.77 (1 H, m), 7.44-7.46 (2 H, m), 7.95-7.97 (2 H, m).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with CHCl3
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-7731b85f0c8349efb162b4a43e332957
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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