Diethyl Ether → (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine-1-carboxylic acid tert-butylester

온도

0 °C

3.77 g (6.15 mmol) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(quinolin-7-yl-methoxy)-piperidine-1-carboxylic acid tert-butylester and 0.93 g (3.12 mmol) of nickel(II) chloride hexahydrate were dissolved in 50 ml of methanol. 0.93 g (24.8 mmol) of sodium borohydride was added at 0° C. in small portions over a period of 30 minutes. The resulting black suspension was then stirred for 1 hour at 0° C., and 2 hours at room temperature. The reaction mixture was slowly poured into a vigorously stirred mixture of 150 ml 5% ammonium chloride solution and 400 ml of ether. After further stirring for 30 minutes, the organic phase was separated. The slightly blue aqueous phase was further extracted 5 times with ether. The combined organic phases were washed twice with distilled water, then dried over magnesium sulphate, filtered and concentrated. The crude product (3.2 g, yellow oil) was chromatographed on silica gel with ethyl acetate/hexane 1:1 to yield 2.92 g (76.9% of theory) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester as a colourless oil; MS: 617 (M+H)+.

1. custom2 hours
2. customat room temperature
3. stirringAfter further stirring for 30 minutes
4. customthe organic phase was separated
5. extractionThe slightly blue aqueous phase was further extracted 5 times with ether
6. washThe combined organic phases were washed twice with distilled water
7. dry with materialdried over magnesium sulphate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product (3.2 g, yellow oil) was chromatographed on silica gel with ethyl acetate/hexane 1:1

ORD 기록

ord-796b872eba784835932264af8e730237

출처 데이터셋

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06274735B1