2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → Dimethyl bicyclo[3.3.1]nonane-1,5-dicarboxylate

Temperature

-78 °C

To a pre-cooled (−78° C.) solution of lithium diisopropylamide (27 mL, 54 mmol) in THF (80 mL) was added DMPU (30.2 g, 236 mol) dropwise, followed by an addition of dimethyl 1-(3-chloropropyl)cyclohexane-1,3-dicarboxylate (11.7 g, 44.7 mmol) in THF (50 mL) within 20 min. The reaction mixture was stirred for 30 min at −78° C. and then allowed to warm up to room temperature over a period of 1.5 h. After quenched with saturated ammonium chloride (100 mL), the mixture was concentrated under reduced pressure. The residue was diluted with water (300 mL) and extracted with dichloromethane (4×100 mL). The combined organic layer was washed with water (100 mL) and brine (100 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 20/1) to afford 8.32 g (82%) of dimethyl bicyclo[3.3.1]nonane-1,5-dicarboxylate as a light yellow oil. ESI-MS m/z: 227 (M+H)+.

1. temperatureto warm up to room temperature over a period of 1.5 h
2. customAfter quenched with saturated ammonium chloride (100 mL)
3. concentrationthe mixture was concentrated under reduced pressure
4. additionThe residue was diluted with water (300 mL)
5. extractionextracted with dichloromethane (4×100 mL)
6. washThe combined organic layer was washed with water (100 mL) and brine (100 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 20/1)

ORD record

ord-d7d32a38d32d4ac7951873608167cdc7

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921370B2