Acetic Acid → HCID 14154747, compound

Participants

Reaction Conditions

Reaction Steps

10N aqueous sodium hydroxide solution (30 cc) is added slowly to a solution of (3S)-3-(acetylthio)quinuclidine (29 g) in methanol (30 cc) maintained at approximately 25° C. The reaction mixture is stirred for 2 hours at a temperature in the region of 20° C. The pH of the reaction mixture is then brought to a value in the region of 9 by adding acetic acid (approximately 10 cc). The mixture obtained is extracted with methylene chloride (3×100 cc). The combined organic phases are dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) and 30° C. The residue obtained is purified by distillation under reduced pressure (970 Pa). (3S)-3-Mercaptoquinuclidine (12 g) is thereby obtained in the form of white crystals which melt at 46° C. and distil at 95° C. under 970 Pa (αD20 =-118°, C=1.1, methanol).

Provenance & Evidence