Water → 1-Pyrrolidinecarboxylic acid, 2-(1-bromo-8-chloroimidazo(1,5-a)pyrazin-3-yl)-, phenylmethyl ester, (2S)-

N-Bromosuccinimide (24.69 mmol, 4.4 g) was added to a stirred solution of (S)-benzyl 2-(8-chloroimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (24.94 mmol, 8.9 g) in DMF (145 mL). The reaction was stirred 3 h at rt. The mixture was poured (slowly) in a stirred mixture of water (145 mL), ethyl acetate (145 mL) and brine (145 mL). The mixture was then transferred into a separating funnel and extracted. The water layer was extracted with 2×145 mL ethyl acetate. The combined organic layers were washed with 3×300 mL water, 300 mL brine, dried over sodium sulfate, filtered and evaporated. The product was purified using silica gel chromatography (ethyl acetate/heptane=3/1 v/v %) to give 8.95 g of (S)-benzyl 2-(1-bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (82.3%).

1. additionThe mixture was poured (slowly)
2. customThe mixture was then transferred into a separating funnel
3. extractionextracted
4. extractionThe water layer was extracted with 2×145 mL ethyl acetate
5. washThe combined organic layers were washed with 3×300 mL water, 300 mL brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe product was purified

ORD 기록

ord-de86550b5cee46648d87cef40e0c81c3

출처 데이터셋

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09290504B2