Ethyl Acetate → 5-(2-Hydroxy-3-pyrrolidin-1-yl-propoxy)-6-methoxy-indan-1-one

HRID 1714441

Reaktionsgleichung

Reaktionsgleichung von HRID 1714441
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[O:13][CH2:14][CH:15]1[CH2:17][O:16]1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(OCC)(=O)C>COCCOC>[OH:16][CH:15]([CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:14][O:13][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:3]=1[O:2][CH3:1])[C:9](=[O:12])[CH2:8][CH2:7]2

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 184458206-Methoxy-5-oxiranylmethoxy-indan-1-one2×

Produkt 1

HCID 184456745-(2-Hydroxy-3-pyrrolidin-1-yl-propoxy)-6-methoxy-indan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 6-methoxy-5-oxiranylmethoxy-indan-1-one (Intermediate M, 2.5 g, 0.0106 mole) and pyrrolidine (0.9 mL, 0.011 mole) was stirred in 50 mL of DME at 50° C. for 5 hrs under Argon. Then, 150 mL of ethyl acetate was added and the solution washed with water (2×). Following extraction with 2N HCl, the aqueous acidic layer was made basic with 3N NaOH and extracted with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was triturated with diethyl ether to yield the title compound. MS m/z 306 (M+H)+.

Aufarbeitung

  1. washthe solution washed with water (2×)
  2. extractionextraction with 2N HCl
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed in vacuo
  7. customThe resulting residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ba2bbb58c36a4f9182ce2bc45a480ccd
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795440B2

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