Triphenylphosphine → 2-[(3S)-1-azabicyclo[2.2.2]octan-3-yloxy]-fluoren-9-one

HRID 553028

Reaktionsgleichung

Reaktionsgleichung von HRID 553028
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:15])[C:4]=2[CH:3]=1.[N:16]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[C@@H:18](O)[CH2:17]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:16]12[CH2:23][CH2:22][CH:19]([CH2:20][CH2:21]1)[C@H:18]([O:1][C:2]1[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5](=[O:15])[C:4]=3[CH:3]=1)[CH2:17]2

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 813862-Hydroxyfluoren-9-oneHCID 914043-Quinuclidinol, (-)-HCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 112204662-[(3S)-1-azabicyclo[2.2.2]octan-3-yloxy]-fluoren-9-oneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a 0° C. mixture of 2-hydroxyfluoren-9-one (196 mg, 1.00 mmol; Aldrich), (3R)-quinuclidin-3-ol (151 mg, 1.20 mmol; Acros), and polymer-bound triphenylphosphine (500 mg, 3 mmol/g; Aldrich) in THF (5 mL) was added diethylazodicarboxylate (200 μL, 1.27 mmol; Aldrich). After 1 h, the reaction mixture was allowed to warm to room temperature and was stirred overnight (16 h). The mixture was filtered through diatomaceous earth, the filter pad rinsed with dichloromethane, and the organic extracts purified twice by flash chromatography (80 g silica gel, eluting with 1-5% of 10% NH4OH/MeOH in CH2Cl2) to afford the title compound (104 mg, 0.340 mmol, 34% yield). MS (DCI/NH3): m/z 306 (M+1)+.

Aufarbeitung

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter pad rinsed with dichloromethane
  3. customthe organic extracts purified twice by flash chromatography (80 g silica gel, eluting with 1-5% of 10% NH4OH/MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-a417337957c34d5e9aa7f3755d9eb191
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951791B2

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