Lithium hydroxide, monohydrate → 4-isopropyl-2-(N-tert-butoxycarbonylpiperidin-3-yl)methoxybenzoic acid

HRID 1787900Notes

Reaction equation

HRID 1787900 reaction equation
[CH:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([O:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH:5]=1)([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:25]([O:24][C:22]([N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([CH2:15][O:14][C:6]2[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:13]=[CH:12][C:7]=2[C:8]([OH:10])=[O:9])[CH2:17]1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68573359Methyl 2-(1-tert-Butoxycarbonylpiperidin-3-ylmethoxy)-4-isopropylbenzoate

Product 1

HCID 685322644-isopropyl-2-(N-tert-butoxycarbonylpiperidin-3-yl)methoxybenzoic acidYield 83.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

The methyl 4-isopropyl-2-(1-tert-butoxycarbonyl-piperidin-3-ylmethoxy)benzoate (1.53 g, 3.90 mmol) was dissolved in THF (15 mL). Then LiOH.H2O (0.36 g, 8.58 mmol) in water (5 mL) was added. The mixture was heated at 65° C. for 24 h. The reaction mixture was concentrated in vacuo and then redissolved in a mixture of EtOAc (100 mL) and cold dilute HCl. The mixture was shaken in a separatory funnel. The layers were separated and the organic layer was washed with cold water (100 mL), dried (MgSO4), and concentrated to give 1.23 g of the title compound as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in a mixture of EtOAc (100 mL) and cold dilute HCl
  3. customThe layers were separated
  4. washthe organic layer was washed with cold water (100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-64265ceffcb246c196f3dc6e771ef307
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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