Trifluoroacetic acid → dimethyl (S)-4-(2-pyrrolidinylmethoxy)isophthalate

HRID 354302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354302
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[C:25]([O:27][CH3:28])=[O:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[C:25]([O:27][CH3:28])=[O:26]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86595076dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]isophthalate

Produkt 1

HCID 86595072dimethyl (S)-4-(2-pyrrolidinylmethoxy)isophthalateAusbeute 53,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]isophthalate (2.01 g, 5.11 mmol), TFA (20 mL), and CH2Cl2 (25 mL) was stirred for 1.5 hr at room temp. The resulting mixture was concentrated in vacuo and made basic with sat. NaHCO3. The mixture was extracted with CH2Cl2, washed with brine, dried over Na2CO3, and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3—MeOH (9:1, v/v) as eluent to give 0.80 g (53%) dimethyl (S)4-(2-pyrrolidinylmethoxy)isophthalate as a yellow oil. 1H-NMR (CDCl3) δ1.71 (m, 1 H), 1.89 (m, 2 H), 2.00 (m, 1 H), 3.05-3.13 (m, 2 H), 3.67 (m, 1 H), 3.90 (s, 3 H), 3.91 (s, 3 H), 4.05-4.18 (m, 2H), 7.00 (d, 1 H, J=8.8 Hz), 8.14 (dd, 1 H, J=2.4, 8.8 Hz), 8.50 (d, 1 H, J=2.4 Hz).

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionThe mixture was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over Na2CO3
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica-gel with CHCl3—MeOH (9:1

Quellen und Nachweise

ORD-Eintrag
ord-b92632aa88fa4a8593452c90b5d6b614
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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