Acetic Anhydride → Aceclidine
Reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[C:10]([O:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)(=[O:12])[CH3:11]Participants
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)).
Workup
- temperaturerefluxed for three hours
- customto yield
Sources & evidence
- ORD record
- ord-cb3ce8ff0e3c41feaf77a13eef5d485a
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05569447
Reaction notes
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