Trifluoroacetic acid → methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate
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]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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)-pirrolidinylmethoxy]benzate (363 mg, quant.) as yellowish oil. The product was used for next reactions without further purification. 1H-NMR (CDCl3) δ1.71-1.83 (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
- concentrationThe mixture was concentrated in vacuo
- additionpoured into aq
- extractionNaHCO3, then extracted with CHCl3
- washThe organic layer was washed with water
- dry with materialdrying over anhydrous Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1f8386478a6240b69e75b399ec420c7a
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06756378B2
Reaction notes
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