3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acids synthesis
- Product Name:3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acids
- CAS Number:209169-30-2
- Molecular formula:C18H16N2O2
- Molecular Weight:292.33
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Yield:209169-30-2 89%
Reaction Conditions:
with glacial acetic acid for 2 h;Reflux;Pictet-Spengler Synthesis;
Steps:
1 4.1.2. General procedure for the preparation of 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acids (2d-f)
General procedure: A mixture of L-tryptophan (10.2 g, 50 mmol), acetic acid (200 ml) and aldehyde (55 mmol, benzaldehyde for 2d, p-fluorobenzaldehydefor 2e, p-methoxy-benzaldehyde for 2f) was refluxed for 2 h, then cooled and adjusted pH to 5 with concentrated ammonium hydroxide. The precipitated product was collected by filtration and washed well with H2O and then dried. Further purification was not necessary and used directly for the next steps. 4.1.2.1
3S-1-Phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2d)
l-Tryptophan was treated with benzaldehyde according to the general procedure to give the desired product 2d as colorless powder in 89% yield.
References:
Lan, Jin-Shuai;Xie, Sai-Sai;Li, Su-Yi;Pan, Long-Fei;Wang, Xiao-Bing;Kong, Ling-Yi [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 21,p. 6089 - 6104]
![N-[(tert-Butoxy)carbonyl]-L-tryptophan](/CAS/GIF/13139-14-5.gif)
13139-14-5
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100-52-7
948 suppliers
$20.37/250g
209169-30-2
5 suppliers
inquiry