تفاعل #164226

معادلة التفاعل

(R)-quinuclidin-3-yl 2-(4-methoxybenzylamino)-2-phenylacetate

2-chloro-1-(thiophen-2-yl)ethanone

→

title compound

المردود 76.1%

(R)-3-[2-(4-methoxy-benzylamino)-2-phenyl-acetoxy]-1-(2-oxo-2-thiophen-2-yl-ethyl)-1-azonia-bicyclo[2.2.2]octane formate formate

المردود 76.1%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىThe residue is first purified by flash chromatography (DCM/MeOH=90/10 to 85/15)
2. 2
   أخرىMeOH is evaporated from the fractions
3. 3
   أخرىcollected
4. 4
   أخرىthe aqueous solution is freeze-dried overnight

الإجراء التجريبي

To a solution of (R)-quinuclidin-3-yl 2-(4-methoxybenzylamino)-2-phenylacetate (C79) (78 mg, 0.21 mmol) in ethyl acetate (2.05 mL), is added 2-chloro-1-(thiophen-2-yl)ethanone (36.2 mg, 0.23 mmol). The colorless solution is stirred at RT overnight. The residue is first purified by flash chromatography (DCM/MeOH=90/10 to 85/15) and then by preparative LC/MS. MeOH is evaporated from the fractions collected and then the aqueous solution is freeze-dried overnight to obtain the title compound as a pale pink oil (44 mg, 36% yield, formate formate anion, mixture of diastereoisomers).

المصدر