反応 #53434

反応方程式

(R)-(+)-3-aminoquinuclidine dihydrochloride

Pyrrolo[1,2-c]pyrimidine-3-carboxylic acid hydrochloride

NaOH

Diphenylphosphinic chloride

→

product

収率 100.0%

N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]pyrrolo[1,2-c]pyrimidine-3-carboxamide Hydrochloride

収率 100.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.WAITAfter 1 day
2. 2
   抽出the mixture is extracted with CHCl3
3. 3
   乾燥The combined organic layers are dried (MgSO4)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The residue is purified by chromatography (Biotage 40S, 90:9:1 CHCl3/MeOH/NH4OH)

実験手順

Pyrrolo[1,2-c]pyrimidine-3-carboxylic acid hydrochloride (0.33 g, 1.66 mmol) and TEA (2.0 mL, 14.35 mmol) are dissolved in 15 mL THF. Diphenylphosphinic chloride (0.47 g, 1.99 mmol) is added dropwise. After 1 h, (R)-(+)-3-aminoquinuclidine dihydrochloride is added and the reaction is allowed to stir at RT. After 1 day, 1N NaOH is added and the mixture is extracted with CHCl3. The combined organic layers are dried (MgSO4), filtered and concentrated. The residue is purified by chromatography (Biotage 40S, 90:9:1 CHCl3/MeOH/NH4OH) to afford 0.45 g (100%) of product. The hydrochloride salt is prepared and recrystallized from CH3CN/Et2O.

出典