Triethylamine → [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-[(E)-4-hydroxybut-1-enyl]phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate

온도

80 °C

Combine [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (1.67 mmol), 3-buten-1-ol (5 mmol), triethylamine (35.8 mmol), and acetonitrile (10 mL) and purge with nitrogen for 10 minutes. To this mixture add palladium acetate (0.17 mmol) and tri-o-tolylphosphine (0.33 mmol). Heat this mixture at 80° C. for 2 hours, then cool to room temperature. Dilute with ethyl acetate (50 mL) and water (50 mL). Separate and wash the organic phase with brine (50 mL). Dry the organics over sodium sulfate, filter, and concentrate under reduced pressure. Purify by flash chromatography (40 g silica gel cartridge) eluting with 5-80% ethyl acetate in dichloromethane to yield the title compound as a tan foam (0.8 g, 1.2 mmol): MS (m/z): 622.0 (M+H).

1. temperaturecool to room temperature
2. customSeparate
3. washwash the organic phase with brine (50 mL)
4. dry with materialDry the organics over sodium sulfate
5. filtrationfilter
6. concentrationconcentrate under reduced pressure
7. customPurify by flash chromatography (40 g silica gel cartridge)
8. washeluting with 5-80% ethyl acetate in dichloromethane

ORD 기록

ord-984fc17bafb24347a38b71f2a84317a5

출처 데이터셋

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09145435B2