1-azabicyclo[2.2.2]octan-3-yl acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. 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) 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. 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) 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A racemic mixture of (RS) 3-quinuclidinol was dissolved in acetic anhydride and refluxed for three hours to yield a racemic mixture of (RS) 3-acetoxy quinuclidine (b.p. 61°-63° C./0.26 mm Hg; 95% yield). To a boiling solution of 28.28 g of this racemic mixture was added a boiling solution of 25.1 g L-(+)-tartaric acid dissolved in 60 ml of 80% ethanol. The solution was allowed to cool to room temperature, then allowed to stand for several hours, yielding crystals of the (+) hydrogen tartrate salt of 3-acetoxy quinuclidine. This salt was recrystallized three times in 80% ethanol to give 16.77 g of colorless crystals (m.p. 93°-96° C. (froths)). In like manner, the free base obtained from the first mother liquor was then treated with R(-)-tartaric acid and recrystallized to yield 14.5 g of colorless crystals of the (-) hydrogen tartrate salt (m.p. 93°-97° C. (froths)). refluxed for three hours to yield

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. 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) 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

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The thus obtained (+) quinuclidinol was esterified with acetic anhydride to yield in a quantitative manner the desired novel (+) 3-acetoxy quinuclidine. The hydrochloride was obtained from a solution of hydrogen chloride in anhydrous ether, M.P. = 175° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A racemic mixture of (RS) 3-quinuclidinol was dissolved in acetic anhydride and refluxed for three hours to yield a racemic mixture of (RS) 3-acetoxy quinuclidine (b.p. 61°-63° C./0.26 mm Hg; 95% yield). To a boiling solution of 28.28 g of this racemic mixture was added a boiling solution of 25.1 g L-(+)-tartaric acid dissolved in 60 ml of 80% ethanol. The solution was allowed to cool to room temperature, then allowed to stand for several hours, yielding crystals of the (+) hydrogen tartrate salt of 3-acetoxy quinuclidine. This salt was recrystallized three times in 80% ethanol to give 16.77 g of colorless crystals (m.p. 93°-96° C. (froths)). In like manner, the free base obtained from the first mother liquor was then treated with R(-)-tartaric acid and recrystallized to yield 14.5 g of colorless crystals of the (-) hydrogen tartrate salt (m.p. 93°-97° C. (froths)). refluxed for three hours to yield

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. 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) 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