四氢-2H-吡喃-4-羧酸甲酯合成路线 （共 26 条）
反应条件
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere
1.2: 22 h / -78 - 25 °C
2.1: diisobutylaluminium hydride / toluene / 19.5 h / -78 °C / Inert atmosphere
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C / Inert atmosphere
View Scheme
参考文献
BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; SRINIVASU, Pothukanuri; BENDER, John A.; LOPEZ, Omar D.; CHEN, Qi; RAMPULLA, Richard A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; MEANWELL, Nicholas A.
Patent: WO2012/21591 A1, 2012 ;
WO 2012/021591 A1
反应条件
1: tetrahydro-pyran-4-carboxylic acid methyl ester With lithium diisopropyl amide in tetrahydrofuran; hexane
0.5 h;
2: carbon dioxide in tetrahydrofuran; hexane
0.25 h;
参考文献
Mihovilovic, Marko D.; Fischer, Thomas C. M.; Stanetty, Peter
Molecules, 2006 , vol. 11, # 5 p. 357 - 364
反应条件
1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h
1.2: 72 percent / tetrahydrofuran; hexane / 0.25 h
2.1: 97 percent / thionyl chloride / CH2Cl2 / 20 °C
View Scheme
参考文献
Mihovilovic, Marko D.; Fischer, Thomas C. M.; Stanetty, Peter
Molecules, 2006 , vol. 11, # 5 p. 357 - 364
反应条件
ammonium chloride; trimethylaluminum in hexane; toluene
T=80°C;
参考文献
Gielen, Heike; Alonso-Alija, Cristina; Hendrix, Martin; Niewoehner, Ulrich; Schauss, Dagmar
Tetrahedron Letters, 2002 , vol. 43, # 3 p. 419 - 421
反应条件
1: tetrahydro-pyran-4-carboxylic acid methyl ester With lithium diisopropyl amide in tetrahydrofuran
T=-70 - 20°C; 0.75 h;
2: methyl iodide in tetrahydrofuran
T=-78 - 20°C; Further stages.;
参考文献
ASTRAZENECA AB
Patent: WO2006/1752 A1, 2006 ;
Location in patent: Page/Page column 91 ;
WO 2006/001752 A1
反应条件
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 0.75 h / -78 - 0 °C / Inert atmosphere
1.2: 22 h / -78 - 25 °C
2.1: diisobutylaluminium hydride / toluene / 19.5 h / -78 °C / Inert atmosphere
View Scheme
参考文献
BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; SRINIVASU, Pothukanuri; BENDER, John A.; LOPEZ, Omar D.; CHEN, Qi; RAMPULLA, Richard A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; MEANWELL, Nicholas A.
Patent: WO2012/21591 A1, 2012 ;
WO 2012/021591 A1
