2743-90-0 | (R,S)-ANATABINE

Introduction
(R,S)-Anatabine is a minor tobacco alkaloid found in Solanaceae plants and can be used as a specific marker for detecting tobacco use.

Specification of CAS: 2743-90-0 (R,S)-ANATABINE

Synthesis of CAS: 2743-90-0 (R,S)-ANATABINE

N-(prop-2-en-1-yl)-1-(pyridin-3-yl)but-3-en-1-amine (5) (58.0 mg, 0.31 mmol) was dissolved in anhydrous CH2Cl2 (3 mL). p-Toluenesulfonic acid monohydrate (118 mg, 0.62 mmol) was added and the mixture was stirred for 10 min. Grubbs’ second-generation catalyst (NHC)(PCy3)Cl2Ru = CHR (25.5 mg, 0.030 mmol, 10 mol %) was added and the resulting mixture was stirred at room temperature for 18 h. The solvent was evaporated and the residue dissolved in EtOAc (30 mL) and 1 M HCl (10 mL) and the phases were separated. The organic layer was extracted additionally with 1 M HCl (3 × 10 mL). The combined aqueous layers were made alkaline (pH = 14) by adding NaOH(s). The basic solution was extracted with EtOAc (4 × 10 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated to yield the crude product that was first stirred with activated carbon and then purified by flash chromatography (eluent: EtOAc:MeOH 95:5 + 1% Et3N, neutral alumina) yielding anatabine (29.8 mg, 0.19 mmol, 60%) as a yellow oil.

Reference:

Saloranta, Tiina; Leino, Reko

[Tetrahedron Letters, 2011, vol. 52, # 36, p. 4619 - 4621]

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