Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(methyl(phenyl)amino)-2-phenylacetate

HRID 77005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77005
Cl.[CH3:2][N:3]([C@H:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([OH:13])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>O1CCOCC1>[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47]([O:12][C:11](=[O:13])[CH:10]([N:3]([CH3:2])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:46]2

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67424971(R)-(methyl-phenyl-amino)-phenyl-acetic acid hydrochloride

Produkt 1

HCID 46840263(R)-quinuclidin-3-yl 2-(methyl(phenyl)amino)-2-phenylacetateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(R)-(Methyl-phenyl-amino)-phenyl-acetic acid hydrochloride (I74) (97 mg, 0.35 mmol), HOBT (107 mg, 0.70 mmol), DCC (144 mg, 0.70 mmol) and (R)-quinuclidin-3-ol (89 mg, 0.70 mmol) are dissolved in dioxane (5 mL) and the mixture is stirred at RT for 15 hours. The white precipitate is filtered and discarded whereas the clear solution is evaporated to dryness. The residue is dissolved in EtOAc and washed with sat. Na2CO3 and then brine. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The resulting crude is purified by flash chromatography on silica gel (DCM/MeOH=97/3 to 95/5) to obtain the title compound as a pale yellow oil (46 mg, 38% yield, mixture of diastereoisomers).

Aufarbeitung

  1. filtrationThe white precipitate is filtered
  2. customis evaporated to dryness
  3. dissolutionThe residue is dissolved in EtOAc
  4. washwashed with sat. Na2CO3
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe resulting crude is purified by flash chromatography on silica gel (DCM/MeOH=97/3 to 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-f0ab57c5bfb5417d846eb3c7603b1f27
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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