Tin atom → HCID 24956148, compound

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Reaction Steps

Ex. 40 (913 mg, 2.033 mmol) was dissolved in hydrogen bromide/glacial acetic acid (33% HBr, 46 ml). Tin powder (2.415 g, 20.344 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 (300 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 pink-coloured wet solid (5.7 g). The mixture was extracted with methylene chloride (3×30 ml). The combined organic phases were dried with Na2SO4 and filtered and the volatile constituents were removed completely in vacuo. A yellow solid (776 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-(cyclohexylmethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine less polar diastereoisomer) (472 mg, contaminated) and the more polar diastereoisomer (269 mg, 32%, m.p.: 195-198° C.) were obtained as white solids.

Provenance & Evidence