Methanol → rac-(1R*,2R*,4R*)-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid

HRID 220296Notes

Reaction equation

HRID 220296 reaction equation
C([O:5][C:6](=[O:22])[CH2:7][C:8]1([OH:21])[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]2[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(C)(C)C.O[Li].O.O.CO>CCO>[OH:21][C:8]1([CH2:7][C:6]([OH:22])=[O:5])[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH:10]=[C:11]2[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 77490009rac-(1R*,2R*,4R*)-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid tert.-butyl ester

Product 1

HCID 68412916rac-(1R*,2R*,4R*)-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

276 mg of rac-(1R*,2R*,4R*)-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid tert.-butyl ester were dissolved in EtOH (1.7 mL) and treated with LiOH.H2O (181 mg), H2O (0.55 mL) and MeOH (1.65 mL). The reaction mixture was stirred at rt for 4 days and concentrated in vacuo. The resulting aq. residue was partitioned between water and Et2O. The aq. layer was separated, acidified with 25%-HCl, and extracted with DCM. The organic phase was dried over anh. Na2SO4 and concentrated to give 205 mg of rac-(1R*,2R*,4R*)-(2-hydroxy-5-thiophen-2-yl-bicyclo[2.2.2]oct-5-en-2-yl)-acetic acid as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting aq. residue was partitioned between water and Et2O
  3. customThe aq. layer was separated
  4. extractionextracted with DCM
  5. dry with materialThe organic phase was dried over anh. Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-75741062dc1c49d0a7e70f2d1554473f
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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