Trifluoroacetic acid → HCID 23511901, compound

HRID 350366Notes

Reaction equation

HRID 350366 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][CH3:24])=[O:22])=[CH:17][C:16]=1[O:25][CH3:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:26][O:25][C:16]1[CH:17]=[C:18]([C:21]([O:23][CH3:24])=[O:22])[CH:19]=[CH:20][C:15]=1[C:14]#[C:13][CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512069HCID 23512069, compound

Product 1

HCID 23511901HCID 23511901, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(tert-butoxycarbonyl)-2-[2-(2-methoxy-4-methoxycarbonyl phenyl)ethynyl]pyrrolidine (395 mg, 1.1 mmol) in CH2Cl2 (3 mL) was added TFA (3 mL). The resulting mixture was stirred for 1 hr. The mixture was concentrated in vacuo and made basic by the addition of sat. NaHCO3, and extracted with CHCl3. The extract was washed with H2O, dried over MgSO4, and evaporated to give 238 mg (84%) 2-[2-(2-methoxy4-methoxycarbonylphenyl) ethynyl]pyrrolidine as a yellow oil. 1H-NMR (CDCl3) δ 1.81–2.16 (4 H, m), 2.97–3.17 (2 H, m), 3.91 (6 H, s), 4.13–4.15 (1 H, m), 7.41 (1 H, d, J=8.3 Hz), 7.51 (1 H, s), 7.56 (1 H, d, J=8.3 Hz).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionmade basic by the addition of sat. NaHCO3
  3. extractionextracted with CHCl3
  4. washThe extract was washed with H2O
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-a72262576d27408fa37b76d3468af31f
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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