Triethylamine → HCID 39236853, compound

According to the method described in J. Org. Chem., 2009, 74, 929, bis(norbornadiene)rhodium tetrafluoroborate (0.22 g, 0.59 mmol) and (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.39 g, 0.62 mmol) were added to a mixture of 2-fluorophenylboronic acid (5.37 g, 38.4 mmol) in nitrogen sparged dioxane (30 mL) under nitrogen atmosphere. After 2 hours of agitation at ambient temperature, water was added (4.6 mL) followed by 2-cyclopenten-1-one (3.06 mL, 36.5 mmol) and triethylamine (5.09 g, 36.5 mmol). The agitation was continued for 24 h at 30° C. then the mixture was diluted with heptane (30 mL), MTBE (10 mL), and water (30 mL). The organic layer was separated and washed with water (50 mL). The aqueous layers were combined and extracted with MTBE/heptane (1:2, 50 mL). Combined organic extracts were dried (Na2SO4) and concentrated. Purification by chromatography (SiO2, hexane/20% ethyl acetate) afforded the title compound (3.94 g, 22.1 mmol, 61%). 1H NMR (300 MHZ, DMSO-d6) δ 7.46-7.27 (M, 1H), 7.25-7.05 (M, 3H), 3.56-3.26 (M, 1H), 2.22-1.41 (M, 6H). MS (ESI) m/z 177 (M−H)+.

1. customsparged dioxane (30 mL) under nitrogen atmosphere
2. additionwater was added (4.6 mL)
3. waitThe agitation was continued for 24 h at 30° C.
4. customThe organic layer was separated
5. washwashed with water (50 mL)
6. extractionextracted with MTBE/heptane (1:2, 50 mL)
7. dry with materialCombined organic extracts were dried (Na2SO4)
8. concentrationconcentrated
9. customPurification by chromatography (SiO2, hexane/20% ethyl acetate)

ORD record

ord-eceb166a86b94c719c64183ad087c43f

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802711B2