* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium tetrahydroborate In methanol at 0 - 20℃; for 24 h;
To a stirred solution of dimethyl 3-oxoglutarate (17.7ml, 120.6mmol) in MeOH (315 mL) at 0 °C was added portion wise NaBH4 (3.9g, 102.5 mol). The reaction was allowed to reach room temperature. After 24 h, the reaction mixture was quenched by addition of solid citric acid until pH reached 5 to 6. To the reaction mixture was added silica gel (ca. 1g) and the solvent was distilled off. The residue was purified by column chromatography on silicagel (EtOAc:hexane, 1:1) to afford the dimethyl 3-hydroxyglutarate (19.98g, 94percent)as a colorless oil.
Reference:
[1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 1, p. 172 - 175
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3650 - 3653
[3] Journal of Organic Chemistry, 1988, vol. 53, # 7, p. 1567 - 1569
[4] RSC Advances, 2016, vol. 6, # 27, p. 22737 - 22748
[5] Journal of the American Chemical Society, 2009, vol. 131, # 49, p. 17980 - 17985
[6] Canadian Journal of Chemistry, 1988, vol. 66, # 6, p. 1422 - 1424
[7] Angewandte Chemie - International Edition, 2008, vol. 47, # 50, p. 9743 - 9746
[8] Journal of Organic Chemistry, 1997, vol. 62, # 15, p. 5057 - 5061
[9] Tetrahedron, 1997, vol. 53, # 40, p. 13757 - 13768
[10] Chemische Berichte, 1953, vol. 86, p. 186,188
[11] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1467[12] Chem.Abstr., 1953, vol. 47, p. 5949
[13] Chemische Berichte, 1953, vol. 86, p. 186,188
[14] Journal of the American Chemical Society, 1961, vol. 83, p. 4228 - 4233
[15] Journal of the American Chemical Society, 1969, vol. 91, p. 7359 - 7371
[16] Tetrahedron, 1987, vol. 43, # 1, p. 45 - 58
[17] Journal of Organic Chemistry, 1998, vol. 63, # 9, p. 3037 - 3040
[18] Il Farmaco; edizione scientifica, 1978, vol. 33, # 4, p. 237 - 252
2
[ 67-56-1 ]
[ 32328-03-3 ]
[ 7250-55-7 ]
Reference:
[1] Synlett, 2007, # 3, p. 491 - 493
3
[ 66833-29-2 ]
[ 7250-55-7 ]
Reference:
[1] Il Farmaco; edizione scientifica, 1978, vol. 33, # 4, p. 237 - 252
4
[ 1830-54-2 ]
[ 106-95-6 ]
[ 7250-55-7 ]
[ 111086-20-5 ]
[ 147528-53-8 ]
Reference:
[1] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2260 - 2264
5
[ 1830-54-2 ]
[ 106-95-6 ]
[ 7250-55-7 ]
[ 111086-20-5 ]
Reference:
[1] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2260 - 2264
6
[ 1830-54-2 ]
[ 106-95-6 ]
[ 7250-55-7 ]
[ 147528-53-8 ]
Reference:
[1] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2260 - 2264
With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; at 0 - 20℃; for 24h;Inert atmosphere;
Under N2 atmosphere, to a stirred solution of dimethyl 3-hydroxypentanedioate (40 g,0.23 mol) and <strong>[51479-73-3]allyl 2,2,2-trichloroacetimidate</strong> (91.9 g, 0.46 mol) in 1000 mL of 4:1c-hexane/CH2Cl2 at 0 oC was added TfOH (4 mL, 46 mmol). After addition, thereaction mixture was stirred for 24 h at room temperature and then filtered. Thefiltrate was washed with NaHCO3 (2 × 200 mL), dried over Na2SO4 and concentratedunder reduced pressure to give yellow oil. The crude product was purified by flashchromatography using PE/EA 9:1 to give product 14 (45.6 g, 93%) as colourless oil
Nitrogen was introduced into the reaction device in advance for 35min; continued to pass nitrogen, 27.8g of imidazole, 40g of t-butyldimethylchlorosilane and 171mL of dichloromethane were sequentially added to the four-necked flask, and stirred at 28 C for 50min; An 84 mL dichloromethane solution containing 40 g (0.227 mol) of dimethyl 3-hydroxyglutarate was added dropwise to the flask.After that, stirring was continued for 7 hours, followed by gas phase analysis. After sufficient reaction, it was cooled to room temperature under the protection of nitrogen. It was washed twice with 200 mL of distilled water and 200 mL of saturated saline successively, the aqueous phase was extracted with 300 mL of ether, and the organic phase was dried over anhydrous magnesium sulfate overnight, vacuum filtered, and the filtrate was distilled under reduced pressure at 30 C. for 6 h using a rotary evaporator. Get the product.