Methanol → N-trityl-3-[4-(benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7]decan-1-amine

Participants

Reaction Steps

To KH (35%; 0.35 g; 0.003 mole) in THF (8 ml) under N2 and cooled to 0° C. is added N-trityl-3-hydroxytricyclo-[3.3.1.13,7 ]decan-1 -amine (1 g; 0.0025 mole) of all at once. The reaction is stirred for 5 minutes with ice cooling then at room temperature for an hour, developing into a clear yellow solution. Then 4-(benzoxazol-2-yl)benzyl bromide (0.70 g; 0.0025 mole) is added and the reaction cooled in ice for 10 minutes and stirred at room temperature for 4 hours. Methanol is added to quench any KH, then the reaction is filtered and evaporated to dryness. HPLC is used to purify the product (eluting with 10% ethyl acetate/hexane) to obtain N-trityl-3-[4-(benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7 ]decan-1-amine (m.p. 174°-177° C.) which is used directly in step D.

Provenance & Evidence