Trityl chloride → N-trityl-3-hydroxytricyclo-[3.3.1.13,7]decan-1-amine

Participants

Reaction Steps

To 3-hydroxytricyclo[3.3.1.13,7 ]decan-1-amine (5 g; 0.03 mole) dissolved in dichloromethane (140 ml) with gentle heating is added triethylamine (6 g; 0.06 mole) and cooled in an ice bath. Triphenylmethyl chloride (8.30 g; 0.03 mole) in CH2Cl2 (10 ml) is added all at once. The reaction is stirred in an ice bath for 10 minutes, warmed to room temperature and then refluxed for 3 hours. The reaction is then filtered and the filtrate evaporated to dryness. The reaction products are separated on HPLC, using 15% ethyl acetate/hexane and the product is then recrystallized from ethyl acetate/pet. ether to give N-trityl-3-hydroxytricyclo-[3.3.1.13,7 ]decan-1-amine (m.p. 184°-186° C.) which is used directly in step C.

Provenance & Evidence