Methanol → HCID 57602489, compound

HRID 1787891Notes

Reaction equation

HRID 1787891 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:22]=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].CO>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 57602510Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoate

Product 1

HCID 57602489HCID 57602489, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoate (9.133 g, 22.6 mmol), 1 M LiOH (40 mL, 40 mmol), MeOH (30 mL) and THF (90 mL) was heated at 60° C. for 14 h. The reaction mixture was concentrated to one-third of its initial volume, diluted with EtOAc (700 mL), and washed with satd citric acid (3×50 mL), and water (3×50 mL) before it was dried (Na2SO4), filtered, and concentrated to give the title compound (6.90 g, 78%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated to one-third of its initial volume
  2. additiondiluted with EtOAc (700 mL)
  3. washwashed with satd citric acid (3×50 mL), and water (3×50 mL) before it
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c19dc6be78b24ac5b520a14c933ce49f
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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