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CAS No.: | 1129634-44-1 |
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Name: | (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID |
Molecular Structure: | |
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Formula: | C12H19NO4 |
Molecular Weight: | 241.287 |
Synonyms: | (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID;5-Azaspiro[2.4]heptane-5,6-dicarboxylic acid, 5-(1,1-diMethylethyl) ester, (6S)-;(S)-5-(tert-Butoxycarbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid;Ledipasvir side chain |
EINECS: | -0 |
Density: | 1.23±0.1 g/cm3(Predicted) |
Boiling Point: | 377.4±35.0 °C(Predicted) |
Solubility: | Slightly Soluble (3.9 g/L) (25 oC), Calc. |
PSA: | 66.84000 |
LogP: | 1.79850 |
(6S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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Stage #1: (6S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate With lithium hydroxide monohydrate; water In ethanol at 20℃; for 20h; Stage #2: With hydrogenchloride In water pH=2; Ice bath; | 100% |
With water; sodium hydroxide In ethanol for 24h; | 34% |
With water; lithium hydroxide In tetrahydrofuran; methanol at 60℃; for 16h; | |
With water; lithium hydroxide In tetrahydrofuran at 20℃; | 2.4 g |
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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With hydrogenchloride In Isopropyl acetate; water at 0℃; pH=3 - 4; | 100% |
di-tert-butyl dicarbonate
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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Stage #1: (S)-5-azaspiro[2.4]heptane-6-carboxylic acid D-di-p-methylbenzoyltartrate With hydrogenchloride In dichloromethane; water for 0.333333h; pH=2-3; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In dichloromethane; water at 0 - 50℃; pH=10-11; | 100% |
(6S)-1,1-dibromo-5-(tert-butoxycarbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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With leaded bronze CuSn7Pb15 In methanol; N,N-dimethyl-formamide at 25℃; Reagent/catalyst; Solvent; Electrolysis; | 98% |
With N-methyl-N,N,N-triethylammonium methylsulfate In N,N-dimethyl-formamide at 25℃; Electrolysis; | 93% |
With palladium 10% on activated carbon; hydrogen; potassium hydroxide In isopropyl alcohol at 40℃; under 760.051 Torr; Inert atmosphere; | 82% |
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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With sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 4h; | 97% |
di-tert-butyl dicarbonate
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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Stage #1: di-tert-butyl dicarbonate; (S)-5-azaspiro[2.4]heptane-6-carboxylic acid D-tartrate With hydrogenchloride In dichloromethane; water pH=2; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In dichloromethane; water at 0 - 20℃; for 15h; pH=10; | 93% |
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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Stage #1: C13H22BrNO4 With sodium hydride In tetrahydrofuran at 0 - 50℃; for 10h; Stage #2: With sodium hydroxide In tetrahydrofuran; water at 50℃; for 5h; Solvent; Reagent/catalyst; | 92% |
(6S)-5-tert-butyl 6-methyl 1,1-dibromo-5-azaspiro[2.4]heptane-5,6-dicarboxylate
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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With V-50; hypophosphorous acid; triethylamine In water at 100℃; | 79% |
Multi-step reaction with 2 steps 1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1.5 h / 20 °C 2: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / toluene / 7 h / 110 °C View Scheme |
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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With water; lithium hydroxide In 2-methyltetrahydrofuran at 50℃; | 71% |
(S)-6-hydroxymethyl-5-azaspiro[2.4]heptane-5-carboxylic acid tert-butyl ester
(6S)-(5-(tert-butoxycarbonyl))-5-azaspiro[2.4]heptane-6-carboxylic acid
Conditions | Yield |
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With Jones reagent In acetone at 0 - 37℃; for 2h; | 70% |