Tert-butyl-(3-iodopropoxy)-dimethylsilane → 2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one

온도

-78 °C

To a solution of 5-cyclohexyl-4-(4-methoxy-benzyl)-morpholin-3-one (700 mg, 2.3 mmol, 1.0 equiv) in THF (10.0 mL) at −78° C. was added n-BuLi (1.58 mL, 1.6 M in heptane, 2.54 mmol, 1.1 equiv). The resulting solution was stirred at −78° C. for 30 minutes, after which it was added a solution of tert-Butyl-(3-iodo-propoxy)-dimethyl-silane (693 mg, 2.3 mmol, 1.0 equiv) in THF (1.0 mL). The solution was stirred at −78° C. for 30 minutes and 2 hours at room temperature after which it was quenched by addition of sat. aq. NH4Cl solution. The mixture was extracted with EtOAc. The organic layer was combined, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography, EtOAc/heptane 30% to give product 480 mg (yield 44%).

1. stirringThe solution was stirred at −78° C. for 30 minutes and 2 hours at room temperature after which it
2. customwas quenched by addition of sat. aq. NH4Cl solution
3. extractionThe mixture was extracted with EtOAc
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customThe residue was purified by silica gel column chromatography, EtOAc/heptane 30%

ORD 기록

ord-162c6b4c046f4cf6965bc8bdc1fe3606

출처 데이터셋

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09040690B2