Diisopropylamine → 1-Cyano-2-(1-cyano-2-phenyl-1-ethyl)-1,2,3,4-tetrahydronaphthalene

Temperature

-78 °C

To a solution of 3.5 mL (25 mmol) of diisopropylamine in 40 mL of THF at -78° C., under a nitrogen atmosphere, was added n-butyllithium (9.5 mL of a 2.5M solution in THF, 23.7 mmol) and the resultant solution was stirred at -78° C. for 0.5 h. To the stirred solution was slowly added a solution of 2.75 g (21 mmol) of 3-phenylpropiononitrile in 40 mL of THF. The reaction mixture was stirred for 45 min at -78° C. and then a solution of 3.1 g (20 mmol) of 1-cyano-3,4-dihydronaphthalene (the product of Step 1 of Example 9) in 40 mL of THF was added. The reaction mixture was stirred at -78° C. for 0.5 h and then the reaction was quenched by pouring the reaction mixture into saturated aqueous ammonium chloride solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 5.70 g (quantitative yield) of the title compound as a mixture of three diastereomers; MS DCl--NH3M/Z: 287 (M+H)+.

1. stirringThe reaction mixture was stirred for 45 min at -78° C.
2. stirringThe reaction mixture was stirred at -78° C. for 0.5 h
3. customthe reaction was quenched
4. additionby pouring the reaction mixture into saturated aqueous ammonium chloride solution
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with ethyl acetate
7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-5be24c88fc2e4cc8b1960a9fe0a69a5d

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05248677