Methanol → HCID 67956774, compound

HRID 1423419Notes

Reaction equation

HRID 1423419 reaction equation
[N+](C1C=C(C=CC=1)C([O:9][C@@H:10]1[CH2:14][C@@H:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][C@@H:11]1[CH3:23])=O)([O-])=O.CO>C1COCC1.O>[CH2:16]([O:15][C@@H:13]1[CH2:14][C@@H:10]([OH:9])[C@@H:11]([CH3:23])[CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 67955812HCID 67955812, compound

Product 1

HCID 67956774HCID 67956774, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R*,2S*,4S*)-4-(benzyloxy)-2-methylcyclopentyl 3-nitrobenzoate (example 25; 11.5 g; 32.5 mmol) in THF (80.0 mL) and MeOH (40.0 mL) LiOH (1.17 g; 48.7 mmol) dissolved in water (40.0 mL) is added. The reaction mixture is stirred at ambient temperature for one hour and concentrated under reduced pressure. The residue is diluted with water and extracted with dichloromethane. The organic layer is dried over MgSO4, and concentrated under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/tert-BuOMe—80:20 to 50:50) to yield 5.9 g of the title compound as pale yellow oil.

Workup

  1. additionis added
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is diluted with water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is chromatographed on silica gel (cyclohexane/tert-BuOMe—80:20 to 50:50)

Sources & evidence

ORD record
ord-e0bd1b5585be4e7ca074d3d295a353bd
Source dataset
uspto-grants-2015_01
Patent number
US08927557B2

Reaction notes

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