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The reaction of aldehydes/ketones with homopropargylic alcohols in the presence of 1-nButyl-3-methylimidazolium chloroaluminate [bmim]Cl·AlCl 3 (N = 0.56-0.67) ionic liquid generates the 4-chloro-5,6-dihydro-2H-pyran derivatives in excellent yield and in short reaction times.

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Prins cyclization of substituted homoallylic alcohol with aryl/aliphatic aldehyde in the presence of a boron trifluoride etherate and trifluoro acetic acid followed by hydrolysis of the resulting trifluoroacetate give substituted cis 2,4,6-tetrahydropyranol products 1-5(c), then Mitsunobu inversion subsequent methanolysis furnished trans 2,4,6-tetrahydropyranol products 1-5(d) stereoselectively in good yield. Our present work reports the synthesis and characterization of these 1-5(c,d) products.

Rasagiline (1) is indicated as adjunctive therapy and monotherapy for treatment of Parkinson's disease approved by the FDA. During the process development of rasagiline, few processes related impurities were observed along with the final API. These impurities were identified as indanol (2), indanamine (3), allyl (4), keto (7), other isomer (6) and chloro allyl (5,5a) impurities. The present work describes the synthesis of all these impurities and characterized by 1 H NMR and Mass spectral analysis.