Dichloromethane → 2,5-Dihydro-3,6-dimethoxy-2-isopropyl-5-(2'-iodo-4'-hydroxy-5'-formylbenzyl)-(2R,5S)-pyrazine

Temperature

0 °C

A 1M solution of BCl3 in dichloromethane (11.8 mL, 11.8 mmol) was added drop wise to a solution of the methoxybenzyl pyrazine analog 22 (134.80 mg, 0.30 mmol) and stirred at 0° C. under argon. The solution changed in color from the initial orange to light brown and finally to greenish brown. The reaction mixture was stirred for one hour at 0° C. and warmed slowly to room temperature over night. The reaction mixture was poured into ice-water and stirred for 15 min. The mixture was extracted with dichloromethane and the organic phase was dried with Na2SO4. Evaporation of the solvent gave a yellow brown oil which upon flash chromatographic purification provided pure 2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(2′-iodo-4′-hydroxy-5′-formylbenzyl)-(2R,5S)-pyrazine (24) (41.40 mg, 32%).

1. stirringThe reaction mixture was stirred for one hour at 0° C.
2. temperaturewarmed slowly to room temperature over night
3. stirringstirred for 15 min
4. extractionThe mixture was extracted with dichloromethane
5. dry with materialthe organic phase was dried with Na2SO4
6. customEvaporation of the solvent
7. customgave a yellow brown oil which upon flash
8. custompurification

ORD record

ord-7dfe001bc066470aa74f19619728b499

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674101B2