反応 #72738

反応方程式

(−)-5-(2-bromopyrid-5-yl)-1-azabicyclo[3.2.1]octane hydrobromide

potassium cyanide

sodium carbonate

→

expected product

収率 76.9%

(−)-(1-Azabicyclo[3.2.1]oct-5-yl)pyridine-2-carbonitrile

収率 76.9%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   抽出The aqueous phase is extracted with chloroform
2. 2
   乾燥the combined organic phases are dried over sodium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The residue is purified by chromatography on a column of silica gel
6. 6
   洗浄eluting with a mixture of chloroform, methanol and aqueous ammonia in 95/5/0.5 proportions

実験手順

1.5 g (4.3 mmol) of (−)-5-(2-bromopyrid-5-yl)-1-azabicyclo[3.2.1]octane hydrobromide (prepared according to the method described in step 1.2 of Example 1), dissolved in 12 ml of dimethylformamide, 0.42 g (6.46 mmol) of potassium cyanide and 5 g (4.3 mmol) of tetrakis(triphenylphosphine)palladium are successively introduced into a 25 ml reactor. The mixture is then heated at 90° C. for 3 hours and then neutralized with saturated aqueous sodium carbonate solution. The aqueous phase is extracted with chloroform and the combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a mixture of chloroform, methanol and aqueous ammonia in 95/5/0.5 proportions. 0.705 g of expected product is thus obtained in the form of an amorphous solid.

出典