Sodium Bicarbonate → (R/S) 6-(2-Carboxy-1-methyl-ethyl)-3,4-dihydro-2H-quinoline-1-carboxylic Acid 9H-Fluoren-9-ylmethyl Ester

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Reaction Steps

A suspension of (R/S) 3-(1,2,3,4-tetrahydro-quinolin-6-yl)-butyric acid (2.6 g) and sodium bicarbonate (2.2 g) in acetone (40 ml) and water (40 ml) was treated with 2,5-dioxo-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (4.0 g) and the resulting mixture was stirred at room temperature overnight. The mixture was filtered and the filtrate evaporated to low bulk. The residue was treated with dilute hydrochloric acid and the resulting gummy precipitate was extracted into a mixture of tetrahydrofuran, ethyl acetate and dichloromethane. This solution was washed with brine, then dried and then evaporated to give the title compound (5.8 g) as a light brown oil, which solidified on standing. MS (ES+) 464 (MNa+), MS (ES−) 440 (M−).

Provenance & Evidence