Phosphate → HCID 17857979, compound

To a solution of 1-allyl 3-methyl 6-methyl-5,6-dihydro-1,3(2 H)-pyridinedicarboxylate (0.44 g, 1.85 mmol) and bromochloromethane (0.18 ml, 2.8 mmol) in THF (15 ml) was added −90 to −80° C. a solution of n-butyllithium in hexane (1.59M, 1.75 ml, 2.8 mmol) over a 15 minute period. After stirring for additional 40 minutes, the reaction mixture was poured into a mixture of ice (10 g) and phosphate buffer (pH 7.0, 10 ml). After ethyl acetate was added and the mixture was separated with a separating funnel, the aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride, dried over magnesium sulfate and the organic solvent was removed under reduced pressure. The residue was purified by silica gel (25 g) chromatography to give allyl 5-(chloroacetyl)-2-methyl-3,6-dihydro-1(2 H)-pyridinecarboxylate (253 mg, 53%).

1. customthe mixture was separated with a separating funnel
2. extractionthe aqueous layer was extracted twice with ethyl acetate
3. washThe organic layer was washed with a saturated aqueous sodium chloride
4. dry with materialdried over magnesium sulfate
5. customthe organic solvent was removed under reduced pressure
6. customThe residue was purified by silica gel (25 g) chromatography

ORD record

ord-e469b27c730245e9a054175fd8b6139a

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07163936B2