4-Vinylpyridine → (R)-(-)-5'-(2-(4-Pyridyl)ethenyl)spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]

온도

102.5 °C

(R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (295 mg, 1 mmol), 4-vinylpyridine (0.135 mL, 1.25 mmol), palladium(II)acetate (7.2 mg, 0.032 mmol), tri-o-tolylphosphine (38.7 mg, 0.127 mmol), and triethylamine (0.5 mL, 3.6 mmol) in anhydrous acetonitrile (0.5 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 100 to 105° C. for 48 hours, cooled to room temperature, dissolved in chloroform (25 mL), washed with saturated aqueous sodium carbonate (2 mL), dried (MgSO4), and evaporated under reduced pressure. Purification by flash chromatography through silica gel (eluting with ammoniated chloroform/methanol, 95:5), followed by recrystallization from acetone afforded the title compound (230 mg, 0.72 mmol, 72%): electrospray MS (m/z, relative intensity) 320 ([MH]+, 100).

1. additioncontaining a magnetic stir bar
2. custompurged with argon
3. customsealed with a Teflon plug and FETFE O-ring
4. temperaturecooled to room temperature
5. dissolutiondissolved in chloroform (25 mL)
6. washwashed with saturated aqueous sodium carbonate (2 mL)
7. dry with materialdried (MgSO4)
8. customevaporated under reduced pressure
9. customPurification by flash chromatography through silica gel (eluting with ammoniated chloroform/methanol, 95:5)
10. customfollowed by recrystallization from acetone

ORD 기록

ord-34ce5c0d9f7c4dfd97e2ec1e88b787b9

출처 데이터셋

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06706878B2