could be produced through the following synthesis routes.

In a 3-l. round-bottomed flask equipped with a mechanical stirrer and flushed with a slow stream of nitrogen are placed 22 ml. (0.26 mole) of concentrated hydrochloric acid (sp. gr. 1.18), 165 ml. of "deoxygenated" water, and 64 g. (0.5 mole) of 2-ethoxy-3,4-dihydro-2H-pyran (b.p. 62–65°/50 mm., n_D25 1.4378). The mixture is stirred vigorously for 20 minutes and then allowed to stand for 1 hour.

To the resulting colorless solution of glutaraldehyde are added, in order, 350 ml. of water, 50 g. (0.74 mole) of commercial methylamine hydrochloride dissolved in 500 ml. of water, 83 g. (0.57 mole) of acetonedicarboxylic acid dissolved in 830 ml. of water, and a solution of 88 g. (0.25 mole) of disodium hydrogen phosphate dodecahydrate and 7.3 g. (0.18 mole) of sodium hydroxide dissolved in 200 ml. of water by heating. dioxide is evolved, and the pH of the solution, initially 2.5, increases to 4.5 after the mixture has been stirred under nitrogen for 24 hours. Concentrated hydrochloric acid (33 ml.) is added, and the solution is heated on the steam bath for 1 hour to complete the decarboxylation. After the solution has been cooled to room temperature, 75 g. of sodium hydroxide in 100 ml. of water is added, and the basic mixture is extracted with eight 250-ml. portions of methylene chloride. The combined methylene chloride extracts are dried over sodium sulfate, concentrated to about 500 ml., and filtered through a layer of 400 g. of alumina packed in a 50-mm. column. The column is eluted with methylene chloride until about 1.5 l. of eluate has been collected. The eluate is concentrated under reduced pressure to yield crystalline but yellow pseudopelletierine. The solid is sublimed at 40° and 0.3 mm. to yield 47–55.5 g. (61–73%) of crude, nearly colorless pseudopelletierine. The product is dissolved in 100 ml. of boiling pentane, 3 ml. of water is added, and the mixture is boiled until the aqueous layer disappears. After thorough chilling in a refrigerator, the crystals which separate are collected on a filter and washed well with ice-cold pentane. Evaporation of the combined filtrate and washings to 20 ml., followed by filtration and washing, yields a second crop of almost equally pure material. The combined pseudopelletierine hemihydrate weighs 47–55 g. and melts at 47–48.5°. Sublimation of the hemihydrate as described above removes the water of hydration and yields 44–52 g. (58–68%) of pure, colorless pseudopelletierine, m.p. 63–64° (sealed tube). Anhydrous material which has been prepared in this manner does not decompose on storage under dry conditions.