Trityl chloride → N-trityl-5-hydroxytricyclo[3.3.1.13,7]decan-2-amine

Participants

Reaction Steps

5-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (2.0 g; 0.012 mole) is dissolved in 70 ml of dichloromethane with gentle heating. To this is added triethylamine (2.4 g; 0.024 mole) and cooled in an ice bath. To this is added triphenylmethyl chloride (3.34 g; 0.012 mole) in dichloromethane (10 ml) all at once. The reaction is stirred for 10 minutes with ice cooling and then 5 hours at room temperature. The reaction mixture is heated to reflux overnight, cooled, filtered and evaporated to dryness. Purification is accomplished via HPLC (eluting with 20% ethyl acetate/hexane) to obtain N-trityl-5-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (m.p. 166°-170° C.) which is used directly in step E.

Provenance & Evidence