Tin atom → HCID 24956501, compound

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Reaction Steps

Ex. 41 (768 mg, 1.733 mmol) was dissolved in hydrogen bromide/glacial acetic acid (33% HBr, 40 ml). Tin powder (2.060 g, 17.353 mmol) was then added to the mixture in portions at room temperature in the course of 40 min and the mixture was stirred for a further 20 min. The mixture was then diluted with water (100 ml). The mixture was stirred at 5° C. for 1 h. The product precipitated out as the hydrobromide. This was filtered off and washed with water (2×5 ml). 1 N NaOH (50 ml) was added to the beige-coloured moist solid (4.3 g). The mixture was extracted with methylene chloride (3×30 ml). The combined organic phases were dried with Na2SO4 and then filtered. The volatile constituents were removed completely in vacuo. An oil (619 mg) remained. After separation of this mixture by chromatography [silica gel 60 (80 g); ethyl acetate (500 ml), ethyl acetate/methanol 20:1 (525 ml), ethyl acetate/methanol 5:1 (600 ml), ethyl acetate/methanol 2:1 (600 ml)], 4-(3-benzyl-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine (less polar diastereoisomer) (186 mg, 26%, m.p.: 194-199° C.) and the more polar diastereoisomer (241 mg, 34%, m.p.: 205-209° C.) were obtained as beige-coloured solids.

Provenance & Evidence