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5,6,7,8-tetrahydroindolizine-1-carboxylic acid synthesis

3synthesis methods
61009-77-6 Synthesis
Ethyl 5,6,7,8-tetrahydro-1-indolizinecarboxylate

61009-77-6
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5,6,7,8-tetrahydroindolizine-1-carboxylic acid

61009-82-3
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Yield:61009-82-3 79%

Reaction Conditions:

with water;potassium hydroxide in methanol; for 3 h;Reflux;

Steps:

5,6,7,8-Tetrahydro-indolizine-1-carboxylic acid (comp. no. 8b)

To a solution of 5,6,7,8-tetrahydro-indolizine-1-carboxylic acid ethyl ester (2b) (3.0 g, 15.5 mmol) in methanol (46 ml) was added water (23 ml) and potassium hydroxide (6.4 g, 97 mmol) and the mixture was stirred at reflux until complete conversion according to LC/MS (ca. 3 h). 160 ml water was added the mixture was acidified with excess hydrochloric acid. The forming precipitate was filtered off, washed once with water and dried in vacuo to give 2.02 g (79 %) of 5,6,7,8-tetrahydro-indolizine-1-carboxylic acid as white solid. LC/MS (method 5; MS ionization method ES-): Rt = 3.08 min; m/z = 164.06 (M-H").

References:

WO2013/113860,2013,A1 Location in patent:Page/Page column 132