(Hexahydro-1H-pyrrolizin-7A-YL)methanamine → 5-{[(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl)amino]methyl}-1-azabicyclo[3.3.0]octane

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Reaction Steps

Under an atmosphere of argon, a solution of 1-bromo-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene [6.90 g, 19.5 mmol, prepared as described in Example 5-a)] in 138 ml of ethanol was added in dropwise to a solution of 5-aminomethyl-1-azabicyclo[3.3.0]octane (3.3 g, 23.6 mmol) in 35 ml of ethanol at the temperature below 0° C. The reaction mixture was allowed to warm slowly from 0°-20° C. and then stirred at 20°-25° C. for 5 hours. The resulting solution was treated as described in Example 8 to afford 4.0 g (49.8%) of the desired compound, as a pale brown oil.

Provenance & Evidence