1,2-Dichloroethane → 9H-fluoren-9-yl quinuclidine-3-carboxylate

HRID 1910514

Reaktionsgleichung

Reaktionsgleichung von HRID 1910514
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([OH:12])=[O:11])[CH2:3]2.C(Cl)CCl.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.[CH:34]1[C:46]2[CH:45](O)[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1>C1COCC1>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH:45]1[C:46]3[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=3[C:39]3[C:44]1=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:11])[CH2:3]2

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 74318Fluoren-9-olHCID 757711-HydroxybenzotriazoleHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

Produkt 1

HCID 709257749H-fluoren-9-yl quinuclidine-3-carboxylateAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Quinuclidine-3-carboxylic acid hydrochloride (95 mg, 0.50 mmol), EDC (143 mg, 0.74 mmol), triethylamine (242 μl, 1.73 mmol), and HOBT (114 mg, 0.74 mmol) were dissolved in dry THF (5 ml). 9H-fluoren-9-ol (99 mg, 0.54 mmol) was dissolved in dry THF (2 ml) and then added to the reaction mixture. The resulting suspension was stirred at room temperature overnight. The mixture was evaporated, and the crude taken up with EtOAc and washed sequentially with water and sat. NaHCO3. The organic phase was dried over sodium sulfate, filtered. and evaporated under vacuum. The crude was purified by flash chromatography (DCM/MeOH=9/1) to afford 9H-fluoren-9-yl quinuclidine-3-carboxylate (102 mg, racemic mixture).

Aufarbeitung

  1. additionadded to the reaction mixture
  2. customThe mixture was evaporated
  3. washwashed sequentially with water and sat. NaHCO3
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customand evaporated under vacuum
  7. customThe crude was purified by flash chromatography (DCM/MeOH=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-ff77864e6ac94ac28d8fe898269cf041
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604015B2

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