反応 #164187

反応方程式

(R)-(Methyl-phenyl-amino)-phenyl-acetic acid hydrochloride

HOBT

DCC

(R)-quinuclidin-3-ol

→

title compound

収率 38.0%

(methyl-phenyl-amino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

収率 38.0%

溶媒

dioxane

反応条件

後処理

1. 1
   ろ過The white precipitate is filtered
2. 2
   その他is evaporated to dryness
3. 3
   workup.DISSOLUTIONThe residue is dissolved in EtOAc
4. 4
   洗浄washed with sat. Na2CO3
5. 5
   乾燥The organic phase is dried over sodium sulphate
6. 6
   ろ過filtered
7. 7
   その他evaporated to dryness
8. 8
   その他The resulting crude is purified by flash chromatography on silica gel (DCM/MeOH=97/3 to 95/5)

実験手順

(R)-(Methyl-phenyl-amino)-phenyl-acetic acid hydrochloride (I74) (97 mg, 0.35 mmol), HOBT (107 mg, 0.70 mmol), DCC (144 mg, 0.70 mmol) and (R)-quinuclidin-3-ol (89 mg, 0.70 mmol) are dissolved in dioxane (5 mL) and the mixture is stirred at RT for 15 hours. The white precipitate is filtered and discarded whereas the clear solution is evaporated to dryness. The residue is dissolved in EtOAc and washed with sat. Na2CO3 and then brine. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The resulting crude is purified by flash chromatography on silica gel (DCM/MeOH=97/3 to 95/5) to obtain the title compound as a pale yellow oil (46 mg, 38% yield, mixture of diastereoisomers).

出典