4-(Benzoxazol-2-yl)benzyl bromide → HCID 54303745, compound

Participants

Reaction Steps

To KH (35%; 0.43 g; 0.0038 mole) in THF (10 ml) under N2 and cooled in ice is added N-trityl-1-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (1.3 g; 0.0032 mole) and this mixture is stirred in an ice bath for 5 minutes and then at room temperature for an hour. To this mixture is added 4-(benzoxazol-2-yl)benzyl bromide all at once and an immediate yellow suspension develops. The reaction is stirred at room temperature for 4 hours, filtered and the filtrate stripped to dryness to give a solid residue. The components are separated on HPLC, eluting with 8% ethyl acetate/hexane to obtain N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]tricyclo[3.3.1.13,7 ]decan-2-amine (m.p. 208°-210° C.) which is used directly in step C.

Provenance & Evidence