1-(6-Chloro-pyridin-3-yl)-cyclopropanecarboxylic acid synthesis
- Product Name:1-(6-Chloro-pyridin-3-yl)-cyclopropanecarboxylic acid
- CAS Number:854267-90-6
- Molecular formula:C9H8ClNO2
- Molecular Weight:197.62
1006875-85-9
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854267-90-6
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Yield:854267-90-6 100%
Reaction Conditions:
with water;sodium hydroxide in methanol;Reflux;
Steps:
4.17 tert-Butyl (1-(6-chloropyridin-3-yl)cyclopentyl)carbamate (3a) and 2-chloro-5-(1-isocyanatocyclopentyl)pyridine (4a): (Procedure C)
General procedure: A solution of 2a (2.26g, 9.42mmol) in MeOH (19mL) was added a 6.0N solution of sodium hydroxide (9.42mL, 56.5mmol). The reaction mixture was refluxed overnight and was added a 4.0M HCl solution in dioxane (15.0mL, 60mmol) at rt. The solvent was removed under reduced pressure. A solution of the residue in anhydrous t-BuOH (0.20L) with flame dried 4 molecular sieve powder (1.0g) was added diphenyl phosphorazidate (2.45mL, 11.3mmol) and triethylamine (2.64mL, 18.8mmol). The reaction mixture was stirred at rt for 1.0h and then heated under reflux overnight. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography with pre-packed silica gel disposable column to afford the title compound 3a (1.42g, 51%) and 4a (0.63g, 30%).
References:
Zhang, Dehui;Zheng, Hongchao;Wang, Xiaodong [Tetrahedron,2016,vol. 72,# 16,p. 1941 - 1953]
39891-09-3
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854267-90-6
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854267-89-3
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854267-90-6
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39891-09-3
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107-21-1
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854267-90-6
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39891-09-3
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854267-90-6
26 suppliers
$200.00/50mg