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143619-74-3

1-(3-pyridinyl)Cyclopentanecarboxylic acid synthesis

6synthesis methods
Cyclopentanecarboxylic acid, 1-(3-pyridinyl)-, ethyl ester

474542-81-9
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1-(3-pyridinyl)Cyclopentanecarboxylic acid

143619-74-3
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Yield:143619-74-3 80%

Reaction Conditions:

with methanol;water monomer;lithium hydroxide monohydrate at 60; for 8 h;

Steps:

1

A solution of ethyl 1-(pyridin-3-yl)cyclopentane-1 -carboxylate (8.4g, 38.5mmol) in MeOH (60ml) was added to 20% aqueous solution of LiOH (2.5g, 96,2mmol). The reaction mixture was stirred for 8 h at 60°C. Then the solvent was removed by freeze-drying, and the corresponding crude product 'was used for the next step without further purification. Yield 7g (80%). LCMS (C18 column 20 x 2 mm, particle size 2.5 pm, pore size 100A, water-acetonitrile+0.1% TFA, gradient 5 to 87% for 3min, retention time 0.82 min). MS (ESI) m/z 192.1 [MH]+.1H-NMR (400MHz, DMSO-d6): δ (ppm) 1.66-1.70 (m, 4H), 1.85-1.92 (m, 2H), 2.52-2.58 (m, 2H), 7.56 (dd, 1H), 7.98-8.02 (m, 1H), 8.58 (dd, 1H), 8.66 (d, 1 H), 12.66 (br.s,

References:

WO2022/47014,2022,A1 Location in patent:Page/Page column 88; 94; 95