Trifluoroacetic acid → ethyl (E)-4-[2-(2-pyrrolidinyl)ethenyl]benzoate

HRID 350329Notes

Reaction equation

HRID 350329 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1/[CH:13]=[CH:14]/[C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1/[CH:13]=[CH:14]/[C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86595070ethyl (E)-4-[2-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]ethenyl]benzoate

Product 1

HCID 86595069ethyl (E)-4-[2-(2-pyrrolidinyl)ethenyl]benzoateYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl (E)-4-[2-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]ethenyl]benzoate (700 mg, 2.03 mmol) in CH2Cl2 (3 mL) was added TFA (3 mL) and the resulting mixture was stirred for 3 hr. The mixture was concentrated and the residue was made basic by the addition of sat. NaHCO3. The mixture was extracted with CHCl3 (2×100 mL). The combined extracts were dried over Na2CO3 and concentrated in vacuo to give 434 mg (87%) ethyl (E)-4-[2-(2-pyrrolidinyl) ethenyl]benzoate as a brown oil. 1H-NMR (CDCl3) δ 1.39 (3 H, t, J=7.3 Hz), 1.52–2.06 (4 H, series of m), 2.93–2.99 (1 H, m), 3.07–3.13 (1 H, m), 3.74 (1 H, q, J=7.3 Hz), 4.37 (2 H, q, J=7.3 Hz), 6.34 (1 H, dd, J=15.6, 7.3 Hz), 6.54 (1 H, d, J=15.6 Hz), 7.41 (2 H, d, J=8.3 Hz), 7.97 (2 H, d, J=8.3 Hz).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was made basic by the addition of sat. NaHCO3
  3. extractionThe mixture was extracted with CHCl3 (2×100 mL)
  4. dry with materialThe combined extracts were dried over Na2CO3
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d514c189a18d43f1919b6625e52905ea
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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