Trifluoroacetic acid → methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate

HRID 350502Notes

Reaction equation

HRID 350502 reaction equation
C([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@H:9]1[CH2:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[C:13]1([C@@H:12]2[NH:8][C@H:9]([CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=3)[CH2:10][CH2:11]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20737850HCID 20737850, compound

Product 1

HCID 69332954methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzateYield 37.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-[N-Boc-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate (1.28 g, 3.11 mmol) in CH2Cl2 (30 ml) was added trifluoroacetic acid (10 ml) at rt, and the resulting mixture was stirred for 45 min. The mixture was concentrated in vacuo and poured into aq.NaHCO3, then extracted with CHCl3. The organic layer was washed with water, drying over anhydrous Na2SO4, and concentrated in vacuo to give methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinyl methoxy]benzate (363 mg, quant.) as yellowish oil. The product was used for next reactions without further purification. 1H-NMR (CDCl3) δ 1.71–1.83 (m, 2 H), 2.03–2.10 (m, 1 H), 2.15–2.24 (m, 1 H), 3.68–3.74 (m, 1 H), 3.89 (s, 3 H), 4.01–4.09 (m, 2 H), 4.28 (t, J=7.2 Hz, 1 H), 6.95 (d, J=8.8 Hz, 2 H), 7.22–7.27 (m, 1 H), 7.33 (t, J=8.0 Hz, 2 H), 7.42 (d, J=7.6 Hz, 2 H), 8.00 (d, J=8.8 Hz, 2 H); MS (ESI) m/z, 312 (M++H) 353 (M++CH3CN).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionpoured into aq
  3. extractionNaHCO3, then extracted with CHCl3
  4. washThe organic layer was washed with water
  5. dry with materialdrying over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e948042a5024a7a8010f62d3145310f
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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