Acetic Anhydride → Aceclidine

Participants

Reaction Steps

A solution of (RS)-3-quinuclidinol (25 g, 0.2 mmol) in pyridine (100 ml) was treated with acetic anhydride (100 ml), kept at 50° C. for 4 hours and left at room temperature for 15 hours. After removal of the pyridine and excess acetic anhydride under vacuum, the clear light brown oil was then dissolved in water (25 ml) and made slightly alkaline with saturated potassium carbonate. The ester was then extracted with chloroform (5×50 ml) and extracts were dried over K2CO3. After evaporation of the solvent in vacuo the residue was distilled yielding 20.6 g (62%) of (RS)-3-acetoxyquinuclidine as a colorless liquid.

Provenance & Evidence