Tin atom → HCID 24956146, compound

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Reaction Steps

Ex. 39 (438 mg, 1.133 mmol) was dissolved in hydrogen bromide/glacial acetic acid (33% HBr, 25 ml). Tin powder (1.345 g, 11.330 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 moist yellow solid (4.0 g). The mixture was extracted with methylene chloride (3×30 ml). The combined organic phases were dried with Na2SO4 and filtered. The volatile constituents were removed completely in vacuo. An oil (425 mg) remained. After separation of this mixture by chromatography [silica gel 60 (40 g); ethyl acetate (500 ml), ethyl acetate/methanol 4:1 (750 ml)] 4-(3-benzyl-1H-indol-2-yl)-1-butyl-N,N-dimethylcyclohexanamine (less polar diastereoisomer, 210 mg, impure) and the more polar diastereoisomer (178 mg, 40%) was obtained as a yellow oil. The less polar diastereoisomer was purified further: Hot methanol (6 ml) was added and the mixture was left to stand at −10° C. overnight. The colourless solid which separated out (144 mg, 33%, melting point of 72-78° C. and 97-99° C.) was filtered off with suction and washed with cold methanol (2×0.5 ml).

Provenance & Evidence