Lithium Hydroxide → (1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-carboxymethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088209Notes

Reaction equation

HRID 2088209 reaction equation
[OH-:1].[Li+].[CH2:3]([N:10]1[C@@H:15]2[C@H:16]([C:18]3[N:22](CC(OC)=O)[N:21]=[N:20][N:19]=3)[CH2:17][C@@:11]1([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C@H:12]([O:28][CH2:29][C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=1)[CH2:13][CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:50]1[CH2:54][O:53]CC1>O>[CH2:3]([N:10]1[C@@H:15]2[C@H:16]([C:18]3[N:22]=[N:21][N:20]([CH2:50][C:54]([OH:1])=[O:53])[N:19]=3)[CH2:17][C@@:11]1([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C@H:12]([O:28][CH2:29][C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:41])([F:43])[F:42])[CH:31]=1)[CH2:13][CH2:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86586756(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(1-methoxycarbonylmethyl-1H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 86586757(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-carboxymethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octaneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium hydroxide (40 mg, 0.9 mmol) was added to a solution of (1R*,2 R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-methoxycarbonylmethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 144a; 0.6 g, 0.91 mmol) in water (5 ml) and THF (5 ml). The reaction mixture was stirred at room temperature for 30 minutes then partitioned between 5% citric acid solution and ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated to yield the title compound (0.55 g, 94%).

Workup

  1. customthen partitioned between 5% citric acid solution and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-30435fdfb8c046b18293247f143d3f62
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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