Ethylene Oxide → HCID 18381564, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (3.0 g, Example 23a) in anhydrous tetrahydrofuran (100 ml) was cooled to −78° C. under a nitrogen atmosphere. A solution of methyllithium (1.4M in diethyl ether, 4.9 ml) was added over 2 min. The mixture was stirred at −78° C. for 10 min., then a solution tert-butyllithium (1.7M in pentane, 9.3 ml) was added dropwise. The mixture was stirred at −78° C. for a further 10 min., then ethylene oxide (1.0 ml) was added. The resulting solution was stirred at −78° C. for 30 min. then was warmed to 0° C. and stirred for another 6 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (70 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography over silica gel eluting with dichloromethane:ethanol (98:2) to give the subtitle compound as a pale yellow solid (0.89 g).

Provenance & Evidence