反应详情

3.87 g (6-bromonaphthalen-2-yloxy)-tert.-butyldimethylsilane were dissolved in 19 ml THF p.a., 6.0 ml 1.6 M butyl lithium solution in hexane added dropwise with dry ice cooling, briefly stirred, then a solution of 2.00 g 4-benzyloxy-2-dimethylaminomethylcyclohexanone in 20 ml THF p.a. added dropwise and stirred for 1 hour while slowly heating. For working up, 4 ml water were added to the ice bath, the organic phase separated, the aqueous phase extracted twice with diethyl ether, the combined organic phases dried by sodium sulphate, filtered and concentrated. The crude product obtained (5.00 g) was chromatographed with ethyl acetate/methanol (V/V=1:1) on silica gel. 2.20 g 6-(4-benzyloxy-2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-naphthalen-2-ol were obtained and converted into the corresponding hydrochloride (1.33 g) in the same way as in AAV 1.

1. additionadded dropwise
2. stirringstirred for 1 hour
3. temperaturewhile slowly heating
4. customthe organic phase separated
5. extractionthe aqueous phase extracted twice with diethyl ether
6. dry with materialthe combined organic phases dried by sodium sulphate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product obtained (5.00 g)
10. customwas chromatographed with ethyl acetate/methanol (V/V=1:1) on silica gel