N(C(OC(C)C)=O)=NC([O:5][CH:6]([CH3:8])C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:35]1[CH:40]2[CH2:41][CH2:42][N:37]([CH2:38][CH2:39]2)[CH2:36]1.[S:43]1C=CC=C1CC(O)=O>O1CCCC1.C(OCC)C.[OH-].[Na+]>[C:6]([S:43][CH:35]1[CH:40]2[CH2:41][CH2:42][N:37]([CH2:38][CH2:39]2)[CH2:36]1)(=[O:5])[CH3:8]Diisopropyl azodicarboxylate (31.6 cc) is added dropwise in the course of 30 minutes to a solution, maintained at 5° C. under an atmosphere of nitrogen, of triphenylphosphine (42 g) in tetrahydrofuran (300 cc). The suspension obtained in then stirred for 30 minutes at 5° C. A solution of 3-hydroxyquinuclidine (10.2 g) and thiolacetic acid (11.4 cc) in tetrahydrofuran (600 cc) is then added to this suspension, maintained at 5° C., in the course of 30 minutes. The reaction mixture is then stirred for 20 hours at a temperature in the region of 20° C. It is then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The oil obtained is dissolved in ethyl ether (400 cc), and then washed with hydrochloric acid (3×160 cc). The combined aqueous phases are washed with ethyl ether (100 cc) and then neutralized to a pH in the region of 7 by adding sodium bicarbonate. The pH of the solution obtained is then adjusted to about 9 by adding a few drops of 10N aqueous sodium hydroxide solution. The mixture is extracted with methylene chloride (3×200 cc). The combined organic phases are dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 30° C. 3-(Acetylthio)quinuclidine (14.7 g) is thereby obtained in the form of a brown oil [Rf=0.33; eluant: methylene chloride/methanol (90:10 by volume)].
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