Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride. A new synthetic method of this compound is introduced below., Quality Control of (1S,2S)-2-Aminocyclopentanol hydrochloride
To a chilled solution of 4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-4-hydroxy-2-oxobut-3-enoic acid (1) (150 mg, 0.338 mmol) in dimethylformamide (DMF) (2.0 mL), was added hydroxybenzotriazole (HOBT) (50 mg, 0.372 mmol), followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI-HCl, 71 mg, 0.372 mmol) and the mixture was stirred for 30 min. A solution of (1S,2S)-(+)-trans-2-aminocyclopentanol hydrochloride and NaHCO3 (31 mg, 0.372 mmol) was added followed by stirring for 2 h at 0-5 C. Cold water was added to the reaction mixture, which was then extracted with ethyl acetate (2 × 20 mL). The combined organic phase was separated, washed with water twice, then once with 1 N HCl solution, and finally with saturated aqueous NaHCO3 solution. Concentration in vacuo afforded the crude product which was passed through a short silica gel column with chloroform as the eluting solvent. The eluent containing the product was concentrated and the resulting residue was triturated with hexanes, which afforded the product as a yellow solid in 117 mg (66%), mp 61-63 C, [alpha]20D[alpha]D20 +41.8 (c 0.01, methanol), UV lambdamax 396 nm (epsilon 14,455, methanol). 1H NMR (CDCl3, 500 MHz): delta 15.33 (br s, 1H), 8.16 (d, 1H, J = 2.0 Hz), 8.08 (s, 1H), 7.61-6.85 (m, 9H), 5.22 (s, 2H), 4.11 (m, 1H), 3.94 (m, 1H), 3.78 (s, 1H), 2.23 (m, 1H), 2.10 (m, 1H), 1.88 (m, 1H), 1.78 (m, 2H), 1.59 (m, 1H). 13C NMR (CDCl3, 125 MHz): delta 181.3, 180.6, 163.4, 163.3, 162.4, 162.1, 162.0, 161.4, 161.3, 160.4, 160.1, 160.0, 159.2, 145.5, 143.9, 142.3, 141.6, 132.4, 132.4, 132.3, 131.5, 131.4, 131.3, 131.3, 131.2, 130.7, 130.6, 125.0, 124.9, 124.8, 122.8, 122.7, 122.5, 122.2, 122.2, 122.1, 122.1, 117.1, 115.9, 115.7, 115.6, 111.9, 111.9, 111.8, 111.7, 104.7, 104.5, 104.3, 98.3, 79.5, 79.3, 61.0, 60.6, 51.5, 47.7, 47.3, 32.9, 32.8, 32.7, 30.8, 30.7, 30.5, 21.7, 21.5. HRMS: calcd for C28H26F3N2O5 (M+H), 527.1794; found 527.1799.
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Reference:
Article; Okello, Maurice; Mishra, Sanjay; Nishonov, Malik; Nair, Vasu; Bioorganic and Medicinal Chemistry Letters; vol. 23; 14; (2013); p. 4112 – 4116;,
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