N~1~-(Pyridin-2-yl)ethane-1,2-diamine → Ethyl 2-[4-[2-(2-pyridylamino)ethylamino]cyclohexyl]acetate

Temperature

-78 °C

To a mixture of 2-(N-[2-(amino)-ethyl]-amino)-pyridine (685 mg, 5 mmol) and ethyl 2-(4-oxocyclohexyl)acetate (786 mg, 4 mmol) was added dichloromethane (4 mL) followed by titanium ethoxide (420 μL, 2 mmol, technical grade). The resulting mixture was stirred for 4 hr then concentrated under reduced pressure. The residue was taken up in methanol (10 mL) and cooled to −78° C. To this solution was added sodium borohydride (228 mg, 6 mmol). On complete addition, the cold bath was removed and stirring continued for 1.25 hr. The mixture was diluted with dichloromethane and poured into saturated sodium carbonate solution (15 mL). The organic phase was separated, dried over magnesium sulfate and concentrated to give the crude title compound as a 6:1 mixture trans:cis isomers. This mixture was used without further purification.

1. concentrationthen concentrated under reduced pressure
2. additionOn complete addition
3. customthe cold bath was removed
4. stirringstirring
5. waitcontinued for 1.25 hr
6. additionThe mixture was diluted with dichloromethane
7. additionpoured into saturated sodium carbonate solution (15 mL)
8. customThe organic phase was separated
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated

ORD record

ord-a05e7165855e4d57b7d586fd1d601cec

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08912169B2