Acetic Anhydride → Aceclidine

HRID 273676Notes

Reaction equation

HRID 273676 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]>N1C=CC=CC=1>[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

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15381(+-)-3-Quinuclidinol

Product 1

HCID 1979AceclidineYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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.

Workup

  1. waitleft at room temperature for 15 hours
  2. customAfter removal of the pyridine and excess acetic anhydride under vacuum
  3. dissolutionthe clear light brown oil was then dissolved in water (25 ml)
  4. extractionThe ester was then extracted with chloroform (5×50 ml) and extracts
  5. dry with materialwere dried over K2CO3
  6. customAfter evaporation of the solvent in vacuo the residue
  7. distillationwas distilled

Sources & evidence

ORD record
ord-9f45afddec244ec5897cbd1db932d30d
Source dataset
uspto-grants-1995_02
Patent number
US05387409

Reaction notes

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