Sodium Hydroxide → 3-{1-[(Tert-butoxy)carbonyl]pyrrolidin-3-yl}benzoic acid

HRID 2202031Notes

Reaction equation

HRID 2202031 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[OH-].[Na+]>CCO.O>[C:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][CH:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([OH:4])=[O:2])[CH2:12]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90239134Tert-butyl 3-(3-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate

Product 1

HCID 534066233-{1-[(Tert-butoxy)carbonyl]pyrrolidin-3-yl}benzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
29 °C

Procedure

To a solution of tert-butyl 3-(3-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate (210 mg, 0.7 mmol) in EtOH (4 ml) was added a solution of NaOH (56 mg, 1.4 mmol) in H2O (1 ml) at 29° C. The mixture was stirred for 30 min at 29° C. The mixture was concentrated and the residue was treated with water and extracted with EA. The water layer was treated with 2N HCl until pH=3, extracted with EA and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification (200 mg, Yield 98.0%).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with water
  3. extractionextracted with EA
  4. additionThe water layer was treated with 2N HCl until pH=3
  5. extractionextracted with EA
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-78e53650410e43669a2973464651645a
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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