1,4-Dibromobenzene → tert-Butyl(3aR,6aR)-1-(4-bromophenyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

온도

140 °C

tert-Butyl(3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (1, 1.5 g, 7.0 mmol), 1.4-dibromobenzene (2.8 g, 20.4 mmol), Pd2(dba)3 (275 mg, 0.3 mmol), BINAP (375 mg, 0.6 mmol) and sodium tert-butoxide (1.93 g, 20.0 mmol) were placed in glass microwave tubes and then purged three times with N2 gas, followed by the addition of toluene (45 mL). The mixture was heated to 140° C. for 15 minutes in a microwave reactor. The mixture was then cooled to room temperature, was filtered, and the crude mixture was purified via chromatography (SiO2, 0-25% ethyl acetate:hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3): δ=7.30 ppm (m, 2H), 7.39 (m, 2H), 4.11 (m, 1H), 3.57 (m, 3H), 3.31 (m, 3H), 2.99 (m, 1H), 2.15 (m, 1H), 1.92 (m, 1H), 1.43 (s, 9H). MS (ESI, M+1): 310.9.

1. custompurged three times with N2 gas
2. additionfollowed by the addition of toluene (45 mL)
3. temperatureThe mixture was then cooled to room temperature
4. filtrationwas filtered
5. customthe crude mixture was purified via chromatography (SiO2, 0-25% ethyl acetate:hexanes)

ORD 기록

ord-922d3082846945a38837d1de7079dd7e

출처 데이터셋

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07728031B2