반응 #57344

반응 방정식

Sodium hydride

indan-2-ol

(S)-2-Methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

→

indanyl ether

수율 17.5%

(S)-2-(Indan-2-yloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

수율 17.5%

용매

N,N′-dimethylformamide

DMF

반응 조건

후처리

1. 1
   기타dried flask
2. 2
   온도to maintain 0° C
3. 3
   workup.STIRRINGThe reaction is stirred at 60° C. for one hour
4. 4
   온도cooled to 0° C.
5. 5
   기타quenched with brine
6. 6
   workup.ADDITIONdiluted with EtOAc
7. 7
   세척washed repeatedly with brine (6×)
8. 8
   기타dried
9. 9
   농축concentrated in vacuo
10. 10
    기타The residue is purified by chromatography on SiO2 (5% EtOAc/Hexanes)

실험 절차

Sodium hydride (60%) (0.6 g, 14.4 mmol) is added to a flame dried flask charged with indan-2-ol (0.965 g, 7.2 mmol) and N,N′-dimethylformamide (DMF) (20 mL), cooled to 0° C. under N2 and stirred for 30 minutes. A solution of (S)-2-Methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (P) (1 g, 3.6 mmol) in DMF (5 mL) is added dropwise to the reaction mixture in such a manner as to maintain 0° C. The reaction is stirred at 60° C. for one hour, cooled to 0° C., quenched with brine, diluted with EtOAc, washed repeatedly with brine (6×), dried and concentrated in vacuo. The residue is purified by chromatography on SiO2 (5% EtOAc/Hexanes) to give 0.20 g of indanyl ether (Q) as a clear colorless oil: LCMS (ES) 340.17 (MNa+).

출처