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

HRID 644181Notes

Reaction equation

HRID 644181 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-d51d157d170941b8b14ae951bda8697d
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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