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| Yield | Reaction Conditions | Operation in experiment |
| 58% |
With ruthenium trichloride; sodium periodate In water; ethyl acetate; acetonitrile at 5 - 39℃; Industry scale |
A 22-L, 3-neck, round bottom flask was equipped with a mechanical stirrer, a J-KEM temperature controller, and anitrogen inlet. The flask was charged with norbornene (200 g, 2.123 mol), ethyl acetate(1.95 L), and acetonitrile (1.95 L). The reaction mixture was cooled to 5 °C using anacetone/dry ice bath. Ruthenium trichloride (9.69 g, 46.72 mmol) was added in oneportion followed by the slow addition of a suspension of sodium periodate (1.816 kg,8.707 mol) in water (2.925 L) over 30 min. The reaction slowly began to exotherm and was monitored to keep the temperature between 10 °C and 15 °C. After 90 min thereaction mixture suddenly thickened to the point where stirring was difficult andexothermed rapidly up to 39 °C (a large amount of dry ice was added to the cooling bath to control the exotherm). The reaction mixture was allowed to cool to 20 °C, the dryice/acetone bath was removed, and the mixture was stirred at room temperature overnight.The solids were removed by filtration through a pad of celite and the filtrate wasconcentrated to a solid which was triturated with hexane (2 L), filtered, and rinsed with hexane (2 x 500 mL) to yield 195 g (58percent) of cyclopentane-l,3-dicarboxylic acid.1H NMR (500 Hz, DMSO-<3/4) δ ppm 12.07 (s, 2H), 2.66-2.73 (m, 2H), 2.06-2.12 (m, 1H), 1.85-1.89 (m, 1H), 1.72-1.85 (m, 4H). |
| 53% |
With sodium periodate; water In chloroform at 20℃; for 48.00 h; |
A mixture of commercially available norbonene (15 g) and RuCl3 (0.3 g) in CHCl3 (100 mL) was stirred at room temperature for 5 min. Then a solution OfNaIO4 (163 g) in H2O (1200 mL) was added and the mixture was stirred at room temperature for 2 d. The mixture was filtered through a pad of celite.(R). and the organic phase was separated. The aqueous phase was saturated with NaCl and extracted with EtOAc (3 x 500 mL). The combined organic phases were treated with MgSO4 and charcoal, filtered and concentrated to afford the crude title compound as thick slightly purple liquid (13.5 g, 53percent). [MH]+ = 159. |
Reference：
[1] Tetrahedron Letters, 2005, vol. 46, # 18, p. 3201 - 3203
[2] Russian Journal of Applied Chemistry, 2011, vol. 84, # 2, p. 236 - 242
[3] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3123 - 3126
[4] Australian Journal of Chemistry, 1985, vol. 38, # 11, p. 1705 - 1718
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 10, p. 3480 - 3491
[6] Patent: WO2012/145569, 2012, A1. Location in patent: Page/Page column 179
[7] Patent: WO2006/128184, 2006, A2. Location in patent: Page/Page column 167
[8] Journal of Organic Chemistry, 1993, vol. 58, # 17, p. 4745
[9] Journal of Organic Chemistry, 1963, vol. 28, p. 2537 - 2541
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