8-Azabicyclo(3.2.1)octan-3-ol, 8-methyl-, 3-methanesulfonate → [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanylmethanethioic S-acid

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Reaction Steps

Tropine-3-mesylate (243.6 g, 1.11 mol) and sodium ethylxanthate (245.1 g, 1.70 mol) were added to stirred toluene (1.25 L) at 36° C. under nitrogen. The mixture was reheated to 35-37° C. (from 30° C.) where it was maintained overnight (˜18 h). The oilbath was removed and water (500 mL) added. After 2 h stirring the mixture was filtered and the phases separated. The toluene phase was washed with deionised water (1×500 mL, 1×300 mL). The yield was found to be 192.36 g, 70.6%, based on 14.42% w/w in solution, by LC analysis against a reference standard. The solution was stored at 4° C. prior to use in Step 4a.

Provenance & Evidence