Phosphate → HCID 11821251, compound

Participants

Reaction Steps

To a solution of 1-allyl 4-ethyl (6S)-6-methyl-3,6-dihydro-1,4(2 H)-pyridinedicarboxylate (200 mg, 0.79 mmol) and bromochloromethane (0.082 ml, 1.3 mmol) in THF (4 ml) was added at −90° C. a solution of n-butyllithium in hexane (1.59M, 0.74 ml, 1.2 mmol). Twenty minute later, the reaction mixture was poured into a mixture of ice (5 g) and phosphate buffer (pH 7.0, 10 ml). To the solution was added ethyl acetate and after separating the mixture with a separating funnel, the aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and the organic solvent was removed under reduced pressure. The residue was purified by silica gel chromatography to give allyl (6S)-4-(chloroacetyl)-6-methyl-3,6-dihydro-1(2 H)-pyridinecarboxylate (167 mg).

Provenance & Evidence