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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 8
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Original Articles

Practical and Scalable Synthesis of Ethyl (R)-Piperidine-3-acetate

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Pages 1137-1145 | Received 21 Sep 2010, Published online: 22 Dec 2011

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  • In view of the weak UV absorption, the optical purity of (R)-1 was determined by HPLC analysis of corresponding N-benzyl derivative. The N-benzyl derived (R)-1 (122 mg, 78% yield) was obtained by treatment of (R)-1 (100 mg, 0.6 mmol) with benzyl chloride (75 mg, 0.6 mmol) in the presence of K2CO3 (165 mg, 1.2 mmol) in CH3CN (5 mL) under reflux for 4 h. N-benzyl derived (S)-1 was also made similarly. HPLC analysis results from the N-benzyl derivatives of (R)-1 and (S)-1: (R)-1: 99.2% ee, retention time: t R = 5.04 min; (S)-1: 100% ee, retention time: t R = 4.14 min. Daicel Chirapak AD-H, detection wavelength = 210 nm, flow rate = 1.0 mL/min, n-hexane:EtOH:diethylamine = 95:5:0.1.

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