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Triethylamine → (3R)-3-[2-Benzyl-6-(3,3-ethylenedioxypyrrolidine-1-yl]-3-pyridyl]ethynyl-3-quinuclidinol

HRID 1359360
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Reaktionsgleichung

Reaktionsgleichung von HRID 1359360
[CH2:1]([C:8]1[C:13](I)=[CH:12][CH:11]=[C:10]([N:15]2[CH2:19][CH2:18][C:17]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:16]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([C@:26]1([OH:34])[CH:31]2[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]2)[CH2:27]1)#[CH:25].C(N(CC)CC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[CH2:1]([C:8]1[C:13]([C:25]#[C:24][C@:26]2([OH:34])[CH:31]3[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]3)[CH2:27]2)=[CH:12][CH:11]=[C:10]([N:15]2[CH2:19][CH2:18][C:17]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:16]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 946095(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 219422862-Benzyl-3-iodo-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine

Produkt 1

HCID 59077796(3R)-3-[2-Benzyl-6-(3,3-ethylenedioxypyrrolidine-1-yl]-3-pyridyl]ethynyl-3-quinuclidinolAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3.0 g of 2-benzyl-3-iodo-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridine, 1.07 g of (3R)-3-ethynyl-3-quinuclidinol, 82 mg of tetrakis(triphenylphosphine)palladium (0), 68 mg of cuprous iodide, 2.0 ml of triethylamine and 7 ml of methanol was stirred at room temperature overnight in a nitrogen atmosphere. The reaction solution was partitioned between aqueous dilute ammonia-ethyl acetate, washed with washed with water, dried over anhydrous magnesium sulfate and then concentrated. 10 ml of tetrahydrofuran was added to the residue to dissolve under heating, and to the mixture was added 15 ml of ethyl acetate. The mixture was filtered through 10 g of NH-silica gel, washed with ethyl acetate, and concentrated. The residue was crystallized from ethyl acetate, to give 2.79 g of the target compound.

Aufarbeitung

  1. customThe reaction solution was partitioned between aqueous dilute ammonia-ethyl acetate
  2. washwashed
  3. washwith washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. addition10 ml of tetrahydrofuran was added to the residue
  7. dissolutionto dissolve
  8. temperatureunder heating
  9. additionto the mixture was added 15 ml of ethyl acetate
  10. filtrationThe mixture was filtered through 10 g of NH-silica gel
  11. washwashed with ethyl acetate
  12. concentrationconcentrated
  13. customThe residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2d088844882042ffb72b6f09a20e2993
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06599917B1

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