Allyl bromide → HCID 19697572, compound

Participants

Reaction Steps

0.5 g of a potassium hydride suspension (20% in oil) is added to a solution of 0.6 g of 1-tert-butoxycarbonyl-3(R,S)-hydroxymethyl-1,2,3,4-tetrahydroquinoline in 7 ml of tetrahydrofuran at 0° C., the mixture is stirred for 30 min and 0.58 ml of allyl bromide is then added. After the mixture has been stirred at 0° C. for 45 min, it is worked up in the customary manner and the crude product is purified over 50 g of silica gel (mobile phase F). 1-Tert-butoxycarbonyl-3(R,S)-allyloxymethyl-1,2,3,4-tetrahydroquinoline is obtained as a colourless oil (Rf (F)=0.40), which is then reacted analogously to Example 20a). Purification by means of FC over 50 g of silica gel with methylene chloride as the mobile phase gives 3(R,S)-allyloxymethyl-1,2,3,4-tetrahydroquinoline: Rf (F)=0.40; MS: M+ =203.

Provenance & Evidence