Methanol → Tert-butyl 4-(4-chloro-3-methylphenyl)-2-methoxypyrrolidine-1-carboxylate

Synthesized according to General Procedure 2. To a stirred solution of tert-butyl-2,5-dihydro-1H-pyrrole-1-carboxylate (2.5 g, 14.8 mmol) in methanol (75 mL) under N2 at RT was added 4-chloro-3-methylbenzenediazonium tetrafluoroborate (5.3 g, 22.2 mmol), followed by the addition of palladium(II) acetate (336 mg, 1.50 mmol). The resulting solution was stirred at RT for 1 hour, diluted with ethyl acetate (375 mL) and partitioned with saturated aqueous NaHCO3 solution (150 mL). The organic layer was removed and washed with saturated aqueous NaHCO3 solution (150 mL), brine (150 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was dried under vacuum to afford tert-butyl 4-(4-chloro-3-methylphenyl)-2-methoxypyrrolidine-1-carboxylate (4.25 g, 13.0 mmol, 88% yield) as a brown oil. The crude product was used without any further purification in the next reaction step. 1H-NMR (400 MHz, DMSO-d6) δ 7.35-7.26 (m, 2H), 7.16 (dd, J=1.9, 8.2 Hz, 1H), 5.20-5.05 (m, 1H), 3.70-3.63 (m, 1H), 3.54-3.45 (m, 1H), 3.28 (s, 3H), 3.21-3.10 (m, 1H), 2.30 (s, 3H), 2.10-1.98 (m, 2H) and 1.47 (s, 9H) ppm.

1. customSynthesized
2. custompartitioned with saturated aqueous NaHCO3 solution (150 mL)
3. customThe organic layer was removed
4. washwashed with saturated aqueous NaHCO3 solution (150 mL), brine (150 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated under reduced pressure
7. customThe residue was dried under vacuum

ORD 기록

ord-224ab620bc85465b9be276262dfb9981

출처 데이터셋

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08343763B2