Trifluoroacetic acid → methyl 4-[(2S,4S)-4-methoxy-2-pyrrolidinyl]methoxybenzoate

HRID 354429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354429
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]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 16093620HCID 16093620, Verbindung

Produkt 1

HCID 16093585methyl 4-[(2S,4S)-4-methoxy-2-pyrrolidinyl]methoxybenzoateAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 4-[(2S,4S)-1tert-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) δ2.16 (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

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted by the addition of CH2Cl2 and 1 N NaOH
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4, which
  6. concentrationwas concentrated in vacuo
  7. customThe residue was chromatographed on silica gel [50 g, CHCl3/MeOH (20/1)]

Quellen und Nachweise

ORD-Eintrag
ord-730e15909c364fcfa8d17a5194815055
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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