Reaction #77892

Reaction equation

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

2-vinylpyridine

→

title compound

Yield 24.0%

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

Yield 24.0%

Conditions

Workup

1. 1
   OtherPurification by flash chromatography through silica gel (eluting with ammoniated ether/methanol, 95:5 to 9:1)
2. 2
   Otherfollowed by recrystallization from acetonitrile

Procedure

(R)-(−)-5′-Bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (150 mg, 0.5 mmol) was treated with 2-vinylpyridine (0.070 mL, 0.65 mmol) in the same way as described in example 16. Purification by flash chromatography through silica gel (eluting with ammoniated ether/methanol, 95:5 to 9:1), followed by recrystallization from acetonitrile produced the title compound (37 mg, 0.12 mmol, 23%): electrospray MS (m/z, relative intensity) 320 ([MH]+, 100).

Source