반응 #837141

반응 방정식

4-[(S)-2-(4-benzyl-phenoxymethyl)-pyrrolidin-1-yl]-butyric acid methyl ester

diisobutylaluminum

AcOH

→

title compound

수율 79.0%

4-[(S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidin-1-yl]-butan-1-ol

수율 79.0%

용매

toluene

toluene

반응 조건

후처리

1. 1
   기타the reaction at −30 to −20° C. for 2 h
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature for 30 minutes
3. 3
   기타formed white solid
4. 4
   여과was filtered
5. 5
   세척washed with acetone
6. 6
   농축The filtrate was concentrated in vacuo

실험 절차

To a solution of 4-[(S)-2-(4-benzyl-phenoxymethyl)-pyrrolidin-1-yl]-butyric acid methyl ester (0.37 g, 1 mmol) in toluene (2 mL) was added 1.5M diisobutylaluminum hrdride in toluene (2 mL, 3 mmol) at −60° C. and then stirred the reaction at −30 to −20° C. for 2 h, followed by addition of 15% AcOH dropwise. The reaction was stirred at room temperature for 30 minutes and formed white solid was filtered and washed with acetone. The filtrate was concentrated in vacuo to yield the title compound as a white solid (0.22 g, 79%); MS; m/z 340.8 (M+H). 1H NMR (400 HMz, CDCl3) δ 1.61-2.26 (m, 8H), 2.79 (m, 1H), 2.85 (m, 1H), 3.25 (m, 2H), 3.42 (m, 2H), 3.54 (m, 1H), 3.68 (m, 1H), 3.75 (m, 1H), 3.92 (s, 2H), 6.82 (d, J=8.8 Hz, 2H), 7.09-7.21 (m, 5H), 7.28 (m, 2H).

출처