Reaktion #77890

Reaktionsgleichung

(R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

azetidine

sodium tert-butoxide

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

→

(R)-(−)-5′-(1-Azetidinyl)spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONcontaining a magnetic stir bar
2. 2
   Sonstigepurged with argon
3. 3
   Sonstigesealed with a Teflon plug and FETFE O-ring
4. 4
   Temperaturcooled to room temperature
5. 5
   workup.DISSOLUTIONdissolved in chloroform (20 mL)
6. 6
   Waschenwashed with brine (3×10 mL)
7. 7
   Trocknendried (MgSO4)
8. 8
   Sonstigeevaporated under reduced pressure
9. 9
   Sonstigepurified by flash chromatography through silica gel (eluting with ammoniated chloroform/methanol 95:5)

Vorschrift

(R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (295 mg, 1 mmol), azetidine (0.101 mL, 1.5 mmol), sodium tert-butoxide (135 mg, 1.4 mmol), tris(dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (62 mg, 0.1 mmol) and anhydrous tetrahydrofuran (9 mL) were combined in a heavy-walled threaded glass tube containing a magnetic stir bar, purged with argon, and sealed with a Teflon plug and FETFE O-ring. The mixture was stirred and heated at 75° C. for 4 hours, cooled to room temperature, dissolved in chloroform (20 mL), washed with brine (3×10 mL), dried (MgSO4), evaporated under reduced pressure, and purified by flash chromatography through silica gel (eluting with ammoniated chloroform/methanol 95:5) to procure the title compound (230 mg, 0.0.85 mmol, 85%) as a light tan solid: chemical ionization MS (m/z, relative intensity) 272 ([MH]+, 56).

Quelle