Trifluoroacetic acid → Methyl 3,5-dichloro-4-(2-pyrrolidinyl)methoxybenzoate
Reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C:15]1[C:24]([Cl:25])=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[Cl:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:26][C:16]1[CH:17]=[C:18]([CH:23]=[C:24]([Cl:25])[C:15]=1[O:14][CH2:13][CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[C:19]([O:21][CH3:22])=[O:20]Participants
Procedure
To a stirred solution of methyl 4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy-3,5-dichlorobenzoate (988 mg, 3.248 mmol) in CH2Cl2 (20 mL) was added TFA (5 mL) at 0° C., and the reaction mixture was stirred at room temp for 2 hr. The solvent was removed under a reduced pressure and the residue was treated with 1N NaOH. The solution was extracted with CHCl3. The extract was washed with brine, dried over Na2SO4, and concentrated under a reduced pressure to afford 672 mg (68%) methyl 3,5-dichloro-4-(2-pyrrolidinyl)methoxybenzoate as a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ1.62-1.69 (m, 1H), 1.78-1.86 (m, 2H), 1.89-199 (m, 1H), 2.92-2.98 (m, 1H), 3.04-3.09 (m, 1H), 3.55-3.60 (m, 1H), 3.91 (s, 3H), 4.01 (dd, J=6.8, 8.8 Hz, 1H), 4.08 (dd, J=4.9, 8.8 Hz, 1H), 7.97 (s, 2H); MS (FAB) m/z 304 (M++1).
Workup
- customThe solvent was removed under a reduced pressure
- additionthe residue was treated with 1N NaOH
- extractionThe solution was extracted with CHCl3
- washThe extract was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under a reduced pressure
Sources & evidence
- ORD record
- ord-5cfa8d6fe7cb458a93b2ff2f8f59338c
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06756378B2
Reaction notes
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