Acetic Acid → 1-Azabicyclo[2.2.2]octane-3-thiol

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Reaction Steps

Sodium methylate (0.5 g) is added to a solution of 3-(acetylthio)quinuclidine (14.5 g) in methanol (150 cc). The reaction mixture is then heated under reflux for 1 hour. Sodium methylate (0.5 g) is added again and the mixture is then heated under reflux for 2 hours. The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. Distilled water (40 cc) is added to the residue obtained, followed by acetic acid (approximately 1 cc) to obtain a pH in the region of 8. The mixture obtained is extracted with methylene chloride (3×20 cc). The combined organic phases are dried over sodium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 30° C. The brown oil obtained is distilled under reduced pressure (920 Pa); the fraction distilling at about 94° C. is collected. 3-Mercaptoquinuclidine (2.8 g) is thereby obtained.

Provenance & Evidence