Hydroboration of 1-allyl-1, 2, 3, 4-tetrahydroquinoline

S Kafka, M Ferles, M Richter

Index: Kafka, Stanislav; Ferles, Miloslav; Richter, Miloslav Collection of Czechoslovak Chemical Communications, 1985 , vol. 50, # 5 p. 1194 - 1200

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Abstract

Abstract Hydroboration of 1-allyl-1, 2, 3, 4-tetrahydroquinoline (I) with triethylamine-borane in the molar ratio 1: 1 afforded a product from which 6, 7-benzo-5-aza-1-boraspiro [4, 5] decane (II) was isolated. Ethanolysis of II gave diethyl 3-(1, 2, 3, 4-tetrahydro-1-quinolyl) propylboronate (III). Acid hydrolysis of the crude hydroboration product and subsequent oxidation with alkaline hydrogen peroxide led to a mixture of 3-(1, 2, 3, 4-tetrahydro-1- ...