1-Methyl-3-pyrrolidinol, (-)- → HCID 86602260, Verbindung

HRID 458894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458894
[CH3:1][O:2][C:3](=[O:17])[C:4]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)[OH:5].[CH3:18][N:19]1[CH2:23]C[C@@H:21](O)[CH2:20]1>C1(C)C=CC=CC=1>[CH3:18][N:19]1[CH2:20][CH2:21][C@@H:1]([O:2][C:3](=[O:17])[C:4]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)([C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)[OH:5])[CH2:23]1

Komponenten

4

Edukt 2

HCID 69513321-Methyl-3-pyrrolidinol, (-)-HCID 669589942-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic acid methyl ester

Produkt 1

HCID 86602260HCID 86602260, VerbindungAusbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

5.0 g (0.021 mol) of 2-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic acid methyl ester were dissolved in 150 ml of dry toluene. To this solution 2.12 g (0.021 mol) of (3R)-1-methylpyrrolidin-3-ol (Intermediate I-19) and 500 mg (0.021 mol) of HNa were added and the mixture was refluxed using a Dean-Stark system for 24 hours. The reaction mixture was cooled, and extracted with HCl 2N. The aqueous layer was basified with K2CO3 and extracted with AcOEt (3×100 ml). The organic layers were combined, dried over Na2SO4 and evaporated to dryness to yield a residue which was purified by chromatography on silica gel eluting with chloroform plus isopropanol (0%→10%). Appropriate fractions were combined and evaporated to give 1.37 g (21%) of the title product as an oil.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. customfor 24 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with HCl 2N
  5. extractionextracted with AcOEt (3×100 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customto yield a residue which
  9. customwas purified by chromatography on silica gel eluting with chloroform plus isopropanol (0%→10%)
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ef7dc212775743209fc7921f7945ddeb
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192978B2

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