Tetrahydrofuran → 3-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

HRID 900772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900772
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=O.C([O-])([O-])=[O:11].[K+].[K+].[CH2:16]1COC[CH2:17]1>>[C:16]([C:3]1([OH:11])[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)#[CH:17]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 5661192-Quinuclidone

Produkt 1

HCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

Versuchsvorschrift

Quinuclidinone (76 g, 0.608 mol) was added to a stirred suspension of lithium acetylide ethylene diamine complex (85.7 g, 0.791 mol) in dry THF (500 ml) under nitrogen, at 0° C. After 16 hours at room temperature, a saturated aqueous solution of K2CO3 was added and the mixture was extracted with THF (3 times). Organic phases were combined, dried over MgSO4 and evaporated under vacuum. The white solid was triturated in ether, filtered and dried to give 3-ethynylquinuclidin-3-ol 47 (56.22 g, 61

Aufarbeitung

  1. extractionthe mixture was extracted with THF (3 times)
  2. dry with materialdried over MgSO4
  3. customevaporated under vacuum
  4. customThe white solid was triturated in ether
  5. filtrationfiltered
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a101d88a6421485dbd305103ed0f1eca
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361668B2

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