2-Cyclopenten-1-one → HCID 89480227, compound

A mixture of 3,4-dichlorophenylboronic acid (488 mg, 2.56 mmol), bis(norbornadiene)rhodium tetrafluoroborate (14.6 mg, 0.0390 mmol) and S-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (25.8 mg, 0.0410 mmol) in dioxane (6.6 mL) was sparged with Ar three times and stirred at rt for 2 h. To the reaction mixture was added water (1.015 mL) followed by the addition of cyclopent-2-enone (200 mg, 2.44 mmol) and TEA (0.340 mL, 2.44 mmol). The reaction mixture was stirred at room for 18 h. The reaction mixture was diluted with DCM, washed with H2O, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography 40 g using hexanes/EtOAc (0-100% over 15 min, flow rate 40 mL/min) to give Intermediate 41A (585 mg, 2.55 mmol, 100% yield) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 1.86-2.02 (1H, m), 2.18-2.38 (2H, m), 2.38-2.55 (2H, m), 2.67 (1H, dd, J=18.2, 7.4 Hz), 3.28-3.49 (1H, m), 7.09 (1H, dd, J=8.0, 2.5 Hz), 7.34 (1H, d, J=1.8 Hz), 7.41 (1H, d, J=8.3 Hz).

1. customwas sparged with Ar three times
2. additionTo the reaction mixture was added water (1.015 mL)
3. stirringThe reaction mixture was stirred at room for 18 h
4. washwashed with H2O
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by flash chromatography 40 g
9. customhexanes/EtOAc (0-100% over 15 min, flow rate 40 mL/min)

ORD record

ord-5b93bdc516e9423d9d3522dd3c26f797

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199946B2