Acetyl chloride → (1R*,2R*,5S*,6R*)-8-Allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(methoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088178Notes

Reaction equation

HRID 2088178 reaction equation
C(Cl)(=O)C.[CH2:5]([N:8]1[C@@H:13]2[C@H:14]([C:16]([O:18][C:19](C)(C)C)=[O:17])[CH2:15][C@@:9]1([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:10]([O:23][CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=1)[CH2:11][CH2:12]2)[CH:6]=[CH2:7]>CO>[CH2:5]([N:8]1[C@@H:13]2[C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:15][C@@:9]1([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:10]([O:23][CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:36])([F:37])[F:38])[CH:26]=1)[CH2:11][CH2:12]2)[CH:6]=[CH2:7]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86586707(1R*,2R*,5S*,6R*)-8-Allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 86586715(1R*,2R*,5S*,6R*)-8-Allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(methoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (5 ml) was cautiously added to methanol (25 ml) and (1R*,2R*,5S*,6R*)-8-allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 94; 1.23 g, 2.16 mmol) dissolved in the resulting solution. After standing for 4 weeks, the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate (25 ml) and saturated aqueous sodium carbonate (2×15 ml), the organic layers dried (MgSO4) and evaporated to leave the title compound as a gum. (1.07 g, 94%).

Workup

  1. dissolutiondissolved in the resulting solution
  2. waitAfter standing for 4 weeks
  3. customthe solvent was removed under reduced pressure
  4. customthe residue partitioned between ethyl acetate (25 ml) and saturated aqueous sodium carbonate (2×15 ml)
  5. dry with materialthe organic layers dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-65ef27df8ea541d6914c077608f4c544
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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