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ChemicalBook CAS DataBase List Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI)

Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI) synthesis

12synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 9 steps
1: 94 percent / LiHMDS / tetrahydrofuran / -78 °C
2: 84 percent / NaN3, 18-Crown-6, DBU / 6 h / Ambient temperature
3: 71 percent / H2 / Pd/C / ethyl acetate / 18 h / 1551.44 Torr
4: 75 percent / TEA / CH2Cl2
5: 90 percent / TFA / H2O
6: 79 percent
7: 40 percent / 5 h / 170 - 180 °C / sealed tube
8: 80 percent / H2 / Pd/C
9: 64 percent / HCl, Dowex 50WX8-100 / Heating

References:

Dominguez, Carmen;Ezquerra, Jesus;Baker, S. Richard;Borrelly, Stephane;Prieto, Lourdes;Espada, Modesta;Pedregal, Carmen [Tetrahedron Letters,1998,vol. 39,# 50,p. 9305 - 9308]

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