Lithium hydroxide, monohydrate → 2-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acid

HRID 1787894Notes

Reaction equation

HRID 1787894 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O>O1CCOCC1.O>[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68532357methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate

Product 1

HCID 685305052-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate (12.9 g, 33 mmol) in p-dioxane (150 mL) was added a solution of LiOH hydrate (2.8 g, 66 mmol) in water (75 mL). The next morning, the solvent was removed in vacuo, and the residue was diluted with water (200 mL) and washed with diethyl ether. The aqueous phase was then adjusted to pH 3 with citric acid and extracted twice with diethyl ether. The combined ether extracts were then washed twice with brine, dried with MgSO4, filtered and concentrated in vacuo to give 11.3 g (91%) of a white foam.

Workup

  1. customThe next morning, the solvent was removed in vacuo
  2. additionthe residue was diluted with water (200 mL)
  3. washwashed with diethyl ether
  4. extractionextracted twice with diethyl ether
  5. washThe combined ether extracts were then washed twice with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f322c29aeb1e485caf31e657dd35d2b8
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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