2-(Dimethylamino)ethanol → 4-(6-(Tributylstannyl)pyridin-2-yl)morpholine

Temperature

2.5 °C

To a solution of 2-dimethylaminoethanol (0.46 mL, 4.56 mmol) in hexane (7.0 mL, HPLC grade) cooled at −5° C. was added drop wise n-BuLi (1.60 M, 5.70 mL, 9.12 mmol) under nitrogen atmosphere. After 30 min at 0° C., 4-pyridin-2-yl-morpholine (0.25 g, 1.52 mmol) in hexane (2.0 mL) was added drop wise. After stirring the reaction mixture for 1 h at 0-5° C., the reaction medium was cooled to −78° C. followed by drop wise addition of tributyl tin chloride (1.03 mL, 3.70 mmol). The resulting reaction mixture was stirred at −78° C. for 30 min and then allowed to stir at 0-5° C. for 2 h. The reaction mixture was then allowed to come to room temperature. After the completion of reaction (TLC monitoring), the reaction mass was cooled to 0° C. and water was added slowly. The aqueous phase was extracted with diethyl ether (3×20 mL). The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness. The crude residue was purified over silica gel (230-400 M) using EtOAc-Hexane (2:98) to provide the compound as yellow oil (0.050 g, 7.20%).

1. temperaturethe reaction medium was cooled to −78° C.
2. customThe resulting reaction mixture
3. stirringwas stirred at −78° C. for 30 min
4. stirringto stir at 0-5° C. for 2 h
5. customto come to room temperature
6. customAfter the completion of reaction (TLC monitoring)
7. temperaturethe reaction mass was cooled to 0° C.
8. extractionThe aqueous phase was extracted with diethyl ether (3×20 mL)
9. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
10. customevaporated to dryness
11. customThe crude residue was purified over silica gel (230-400 M)

ORD record

ord-9af72da288c748a68ace8b7b06f578ae

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977340B2