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

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).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 12 h
3. customevaporated
4. dissolutionThe residue was dissolved in 20 mL of ethanol
5. customevaporated
6. dissolutionThe residue was dissolved
7. customto remove excess NaBH4
8. extractionThe mixture was extracted three times
9. extractionAfterwards, the organic layer was extracted twice
10. extractionextracted three times
11. customThe organic layer was dried
12. customevaporated

ORD record

ord-ae2901b2b0e94ff0ae1bd954319a2f32

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541449B2