(2S,3AS,7aS)-Octahydroindole-2-carboxylic acid
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(2S,3AS,7aS)-Octahydroindole-2-carboxylic acid
structure -
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CAS No:
80875-98-5
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Formula:
C9H15NO2
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Chemical Name:
(2S,3AS,7aS)-Octahydroindole-2-carboxylic acid
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Synonyms:
1H-Indole-2-carboxylic acid,octahydro-,(2S,3aS,7aS)-;1H-Indole-2-carboxylic acid,octahydro-,[2S-(2α,3aβ,7aβ)]-;(2S,3aS,7aS)-Octahydro-1H-indole-2-carboxylic acid;(2S,3AS,7aS)-2-carboxyoctahydroindole;(2S,3aS,7aS)-perhydroindole-2-carboxylic acid;(2S,3AS,7aS)-Octahydroindole-2-carboxylic acid;111821-04-6
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CAS No:
(2S,3AS,7aS)-Octahydroindole-2-carboxylic acid Basic Attributes
169.22
169.22
1592732-453-0
29339900
Characteristics
49.3
-1
Whitish or yellowish crystalline powder
1.1±0.1 g/cm3
267-269 °C @ Solvent: Ethanol
318.6ºC at 760 mmHg
146.5±23.2 °C
1.508
soluble in methanol and water.
Store at 0°C
Safety Information
NONH for all modes of transport
3
36/37/38
26-37
Xn,Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
(2S,3AS,7aS)-Octahydroindole-2-carboxylic acid Use and Manufacturing
Introduce 200 g of the compound obtained in the previous Step, dissolved in acetic acid, and then 5 g of Pt/C 10percent into a hydrogenator. Hydrogenate under a pressure of 5 bars at ambient temperature until the theoretical amount of hydrogen has been absorbed. Remove the catalyst by filtration and then cool to a temperature of from 0 to 5° C. and collect the resulting solid by filtration. Wash the filter cake and dry it to constant weight. (2S, 3aS, 7aS)-Perhydroindole-2-carboxylic acid is obtained in that manner in a yield of 87percent and with an enantiomeric purity of 99percent.In a 1 L autoclave, (S) -indoline-2-carboxylic acid (0.3 mol, 49.0 g) and methanol (600 mL)Then, 4.9 g of 8percent wet palladium carbon wetted with methanol was added, Mechanical agitation. Through the nitrogen replacement air 3 times, And then hydrogen gas replacement nitrogen 3 times, Replace the kettle when the pressure is 0.5Mpa. after finishing, Continue to hydrogen to 5.0Mpa, set the heating temperature at 60 , Maintaining the temperature of the reaction system at 55 to 65 ° C, TLC (developing solvent: chloroform: methanol: triethylamine = 6: 4: 1, ninhydrin)Tracking to the raw point of the reaction is complete. The hydrogen was vented and the hydrogen was replaced with nitrogen three times.Discharge, filter, take the filtrate under reduced pressure, A crude solid was obtained as a white solid. Finally, recrystallization from ethanol, A white solid was obtained in 37.3 g yield, 73.5percent yield, Purity 98.6percent (HPLC),
An intermediate in the synthesis of Perindopril
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(2S,3AS,7aS)-Octahydroindole-2-carboxylic acid
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