Acetic Acid → 1-Azabicyclo[2.2.2]octane-3-thiol

HRID 2291830Notes

Reaction equation

HRID 2291830 reaction equation
C[O-].[Na+].C([S:7][CH:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)(=O)C.C(O)(=O)C>CO>[SH:7][CH:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium Methoxide2×HCID 14154745HCID 14154745, compound

Product 1

HCID 141547461-Azabicyclo[2.2.2]octane-3-thiolYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methylate (0.5 g) is added to a solution of 3-(acetylthio)quinuclidine (14.5 g) in methanol (150 cc). The reaction mixture is then heated under reflux for 1 hour. Sodium methylate (0.5 g) is added again and the mixture is then heated under reflux for 2 hours. The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. Distilled water (40 cc) is added to the residue obtained, followed by acetic acid (approximately 1 cc) to obtain a pH in the region of 8. The mixture obtained is extracted with methylene chloride (3×20 cc). The combined organic phases are dried over sodium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 30° C. The brown oil obtained is distilled under reduced pressure (920 Pa); the fraction distilling at about 94° C. is collected. 3-Mercaptoquinuclidine (2.8 g) is thereby obtained.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureunder reflux for 1 hour
  3. temperaturethe mixture is then heated
  4. temperatureunder reflux for 2 hours
  5. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  6. additionDistilled water (40 cc) is added to the residue
  7. customobtained
  8. customto obtain a pH in the region of 8
  9. customThe mixture obtained
  10. extractionis extracted with methylene chloride (3×20 cc)
  11. dry with materialThe combined organic phases are dried over sodium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 30° C
  14. customThe brown oil obtained
  15. distillationis distilled under reduced pressure (920 Pa)
  16. distillationthe fraction distilling at about 94° C.
  17. customis collected

Sources & evidence

ORD record
ord-79f06c02f01d4cb1a948efdbe09629ef
Source dataset
uspto-grants-1989_01
Patent number
US04798827

Reaction notes

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