Ethanol → (1S,4S,5S)-5-(1-Amino-propyl)-5-phenyl-bicyclo[2.2.1]heptan-2-ol

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Reaction Steps

930 mg (2.8 mmol) of (1S,2S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-bicyclo[2.2.1]heptane-2-carbonitrile (88) were dissolved in 10 mL of anhydrous toluene. Afterwards, 5.7 mL of a 1M solution of ethylmagnesium bromide in THF was added and the mixture was heated under reflux for 12 h. The mixture was then treated with 3 mL ethanol and evaporated. The residue was dissolved in 20 mL of ethanol and 215 mg (5.7 mmol) of NaBH4 was added. The mixture was stirred at ambient temperature for 3 h and then evaporated. The residue was dissolved using 100 mL of water, the pH adjusted to 3 using aqueous HCl-solution to remove excess NaBH4 and then adjusted to pH=12 using saturated aqueous Na2CO3-solution. The mixture was extracted three times using 30 mL of t-butylmethylether each. Afterwards, the organic layer was extracted twice using 20 mL of a 1N aqueous HCl-solution each, the aqueous layer was adjusted to pH>11 using saturated aqueous Na2CO3-solution and extracted three times using 30 mL t-butylmethylether each. The organic layer was dried using MgSO4 and evaporated yielding 200 mg of the desired product 89, used without further purification. Rt=0.58 min (Method 18).

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