Trifluoroacetic acid → methyl 4-[(2S,4S)-4-methoxy-2-pyrrolidinyl]methoxybenzoate
Reaktionsgleichung
C(OC([N:8]1[CH2:12][C@@H:11]([O:13][CH3:14])[CH2:10][C@H:9]1[CH2:15][O:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:14][O:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)[CH2:10]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of methyl 4-[(2S,4S)-1-tert-butoxycarbonyl-4-methoxy-2-pyrrolidinyl]methoxybenzoate (2.38 g, 3.61 mmol) in CH2Cl2 (46 ml) was added TFA (23 ml) at room temperature. After 14 h stirring, the mixture was concentrated in vacuo. The residue was diluted by the addition of CH2Cl2 and 1 N NaOH, and extracted with CH2Cl2. The combined extracts were washed with brine, dried over Na2SO4, which was concentrated in vacuo. The residue was chromatographed on silica gel [50 g, CHCl3/MeOH (20/1)], to give methyl 4-[(2S,4S)-4-methoxy-2-pyrrolidinyl]methoxybenzoate (950 mg, 99%) as a yellow oil. 1H-NMR (CDCl3) δ 2.16 (t, J=5.3 Hz, 1H), 2.72 (s, 1H), 2.95 (d, J=6.8 Hz, 1H), 3.11 (d, J=11.0 Hz, 1H), 3.26 (t, J=1.9 Hz, 3H), 3.52 (br, 1H), 3.84 (d, J=1.7 Hz, 3H), 3.92 (s, 1H), 4.00 (d, J=4.1 Hz, 2H), 6.88 (m, 2H), 7.94 (m, 2H).
Aufarbeitung
- concentrationthe mixture was concentrated in vacuo
- additionThe residue was diluted by the addition of CH2Cl2 and 1 N NaOH
- extractionextracted with CH2Cl2
- washThe combined extracts were washed with brine
- dry with materialdried over Na2SO4, which
- concentrationwas concentrated in vacuo
- customThe residue was chromatographed on silica gel [50 g, CHCl3/MeOH (20/1)]
Quellen und Nachweise
- ORD-Eintrag
- ord-f0cc63a0258d415c99db2e0d17bb5028
- Quelldatensatz
- uspto-grants-2007_02
- Patentnummer
- US07179819B2
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