반응 #164226

반응 방정식

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

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

→

title compound

수율 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

수율 76.1%

용매

ethyl acetate

반응 조건

후처리

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

실험 절차

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).

출처