반응 #164157

반응 방정식

2-(benzylamino)-2-phenylacetic acid

DCC

HOBt

3(R)-quinuclidinol

→

(R)-quinuclidin-3-yl 2-(benzylamino)-2-phenylacetate

수율 52.0%

용매

THF

반응 조건

후처리

1. 1
   기타The solvent is evaporated
2. 2
   세척washed twice with water
3. 3
   건조The organic phase is dried over Na2SO4
4. 4
   여과filtered
5. 5
   기타evaporated to dryness
6. 6
   기타The resulting crude is purified by flash chromatography (DCM/MeOH=98/2, 0.2% NH3(aq.) to 95/5, 0.5% NH3(aq))
7. 7
   기타to give
8. 8
   workup.ADDITIONa mixture of diastereoisomers 1 and 2 of C24 (231 mg, 52% yield, mixture of diasteroisomers)

실험 절차

A mixture of 2-(benzylamino)-2-phenylacetic acid (I23) (0.94 g, 3.90 mmol), DCC (0.97 g, 4.70 mmol), HOBt (0.63 g, 4.07 mmol) and 3(R)-quinuclidinol (1.51 g, 11.7 mmol) in dry THF (30 mL) is stirred at room temperature overnight under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is taken up with EtOAc and washed twice with water. The organic phase is dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by flash chromatography (DCM/MeOH=98/2, 0.2% NH3(aq.) to 95/5, 0.5% NH3(aq)) to give a mixture of diastereoisomers 1 and 2 of C24 (231 mg, 52% yield, mixture of diasteroisomers).

출처