Phosphoric Acid → HCID 18957101, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (±)1-azabicyclo[3.2.1]oct-3-en-3-yl-N-methoxy-N-methylcarboxamide (D8) (0.40 g, 2.0 mmole) in dry tetrahydrofuran (20 ml) was cooled to -70° C., under a nitrogen atmosphere, and treated dropwise over 15 minutes with methyllithium (1.47 ml of a 1.5 m solution in diethyl ether as the complex with lithium bromide, 2.2 mmole). The temperature was maintained at -70° C. for 30 minutes, and then allowed to warm to 0° C. over 1.75h. The reaction was cooled to -20° C. and poured into a 1M solution of orthophosphoric acid (20 ml) cooled below 0° C. The organic layer was separated, and the aqueous phase was saturated with potassium carbonate, and extracted exhaustively with chloroform. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give a pale yellow oil (0.33 g) which was distilled in a kugelrohr at 150° C./0.1 mmHg to give the title compound (D10) as a colourless liquid (0.28 g, 93%).

Provenance & Evidence