Boron trifluoride etherate → (3R)-3-(3-cyclohexyl-3-phenyl-1-propynyl)-1-azabicyclo[2.2.2]oct-3-yl methyl ether

HRID 900780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900780
[CH:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(O)[C:8]#[C:9][C@:10]2([O:18][CH3:19])[CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:19][O:18][C@@:10]1([C:9]#[C:8][CH:7]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 444065731-cyclohexyl-3-((R)-3-methoxyquinuclidin-3-yl)-1-phenylprop-2-yn-1-ol

Produkt 1

HCID 69290748(3R)-3-(3-cyclohexyl-3-phenyl-1-propynyl)-1-azabicyclo[2.2.2]oct-3-yl methyl etherAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

1-cyclohexyl-3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]oct-3-yl]-1-phenyl-2-propyn-1-ol 201 (150 mg, 0.42 mmol) was dissolved under argon in CH2Cl2 (20 ml) and then cooled to −40° C. Neat Et3SiH (203 μL, 1.27 mmol) was added dropwise. After 5 minutes, neat BF3.OEt2 (376 μL, 1.27 mmol) was slowly added to the mixture. After 15 minutes, the reaction was slowly left to room temperature, then quenched with saturated aqueous K2CO3 solution after 45 minutes and diluted with ether. The organic phase was dried over Na2SO4 and evaporated to dryness to give (3R)-3-(3-cyclohexyl-3-phenyl-1-propynyl)-1-azabicyclo[2.2.2]oct-3-yl methyl ether 112 (mixture of diastereomers) as a colorless oil (140 mg, 97%).

Aufarbeitung

  1. waitAfter 15 minutes
  2. waitthe reaction was slowly left to room temperature
  3. customquenched with saturated aqueous K2CO3 solution after 45 minutes
  4. additiondiluted with ether
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-0b1e9707afbd4f38ac9c6a2f3da37b6d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361668B2

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