8-Azabicyclo(3.2.1)octan-3-ol, 8-methyl-, 3-methanesulfonate → [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanylmethanethioic S-acid

HRID 222144Notes

Reaction equation

HRID 222144 reaction equation
[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8](OS(C)(=O)=O)[CH2:9][CH:3]1[CH2:4][CH2:5]2.C([O:17][C:18]([S-:20])=[S:19])C.[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C@@H:3]2[CH2:9][CH:8]([S:19][C:18]([SH:20])=[O:17])[CH2:7][C@H:6]1[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 1419518-Azabicyclo(3.2.1)octan-3-ol, 8-methyl-, 3-methanesulfonateHCID 23690437Sodium ethylxanthate

Product 1

HCID 71776021[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanylmethanethioic S-acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tropine-3-mesylate (243.6 g, 1.11 mol) and sodium ethylxanthate (245.1 g, 1.70 mol) were added to stirred toluene (1.25 L) at 36° C. under nitrogen. The mixture was reheated to 35-37° C. (from 30° C.) where it was maintained overnight (˜18 h). The oilbath was removed and water (500 mL) added. After 2 h stirring the mixture was filtered and the phases separated. The toluene phase was washed with deionised water (1×500 mL, 1×300 mL). The yield was found to be 192.36 g, 70.6%, based on 14.42% w/w in solution, by LC analysis against a reference standard. The solution was stored at 4° C. prior to use in Step 4a.

Workup

  1. customwas reheated to 35-37° C.
  2. custom(from 30° C.) where it
  3. temperaturewas maintained overnight (˜18 h)
  4. customThe oilbath was removed
  5. additionwater (500 mL) added
  6. filtrationwas filtered
  7. customthe phases separated
  8. washThe toluene phase was washed with deionised water (1×500 mL, 1×300 mL)
  9. customwas stored at 4° C.

Sources & evidence

ORD record
ord-f7f12fc225f84d97a311c7f5135f4ddd
Source dataset
uspto-grants-2012_06
Patent number
US08207191B2

Reaction notes

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