Hydrochloric Acid → HCID 11107435, compound

To a solution of 1-allyl 4-tert-butyl (2R)-2-methyl-3,6-dihydro-1,4(2 H)-pyridinedicarboxylate (0.64 g, 2.3 mmol) in methanol (10 ml) was added hydrochloric acid/methanol (10 ml) and the mixture was stirred overnight. Toluene was added thereto and the solvent was removed in vacuo. To the residue were added methanol and toluene, and the solvent was again removed in vacuo. The residue was dissolved in THF (10 ml) and to the solution was added at 0–5° C. a solution of trimethylsilyldiazomethane in hexane (2M, 1.15 ml, 2.3 mmol). Fifteen minutes later 1N hydrochloric acid was added thereto. Ethyl acetate and a saturated aqueous sodium chloride solution were added thereto. The mixture was separated with a separating funnel. The aqueous layer was extracted twice with ethyl acetate. The organic layer was washed twice with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel (20 g) chromatography (hexane/ethyl acetate: 1/6→1/4) to give 1-allyl 4-methyl (2R)-2-methyl-3,6-dihydro-1,4(2 H)-pyridinedicarboxylate (0.31 g)

1. customthe solvent was removed in vacuo
2. additionTo the residue were added methanol and toluene
3. customthe solvent was again removed in vacuo
4. dissolutionThe residue was dissolved in THF (10 ml) and to the solution
5. customThe mixture was separated with a separating funnel
6. extractionThe aqueous layer was extracted twice with ethyl acetate
7. washThe organic layer was washed twice with a saturated aqueous sodium chloride solution
8. dry with materialdried over magnesium sulfate
9. customThe solvent was removed under reduced pressure
10. customthe residue was purified by silica gel (20 g) chromatography (hexane/ethyl acetate: 1/6→1/4)

ORD record

ord-5c849f94d9f44d6cb53fa96bee27e695

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07163936B2