Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI) synthesis
- Product Name:Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1S,2S,5R,6S)- (9CI)
- CAS Number:176199-48-7
- Molecular formula:C8H11NO4
- Molecular Weight:185.18
![Spiro[cyclohexane-1,2'-cyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole]-4'-carboxylic acid, hexahydro-5'-oxo-, ethyl ester, (3'aR,3'bR,4'S,4'aS,5'aR)-](/CAS/20211123/GIF/188885-69-0.gif)
188885-69-0
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176199-48-7
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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]
![Spiro[bicyclo[3.1.0]hexane-2,4'-imidazolidine]-6-carboxylic acid, 2',5'-dioxo-, ethyl ester, (1S,2S,5R,6S)-](/CAS/20210305/GIF/188885-88-3.gif)
188885-88-3
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176199-48-7
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![Spiro[cyclohexane-1,2'-cyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole]-4',5'-dicarboxylic acid, 5'-aminohexahydro-, 4',5'-dimethyl ester, (3'aR,3'bR,4'R,4'aS,5'R,5'aS)-](/CAS/20211123/GIF/219762-21-7.gif)
219762-21-7
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176199-48-7
83 suppliers
$29.00/1mg
176199-48-7
83 suppliers
$29.00/1mg
![Spiro[cyclohexane-1,2'-cyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole]-4'-carboxylic acid, hexahydro-5'-hydroxy-5'-(trichloromethyl)-, ethyl ester, (3'aR,3'bR,4'S,4'aS,5'S,5'aR)-](/CAS/20211123/GIF/219762-17-1.gif)
219762-17-1
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176199-48-7
83 suppliers
$29.00/1mg