Hydrochloric Acid → 1-Benzyl-4-(2-methylphenyl)pyrrolidine-3-carboxylic acid

HRID 1805946Notes

Reaction equation

HRID 1805946 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:10]([C:20]([O-:22])=[O:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:10]([C:20]([OH:22])=[O:21])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86761748HCID 86761748, compound

Product 1

HCID 533948381-Benzyl-4-(2-methylphenyl)pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To 1-Benzyl-4-(2-methylphenyl)pyrrolidine-3-carboxylate (0.685 g, 2.214 mmol) in THF/MeOH/H2O (5 ml) was added 2N NaOH (3.32 ml, 6.64 mmol). The solution was stirred for 12 hours at room temperature and was acidified to pH1-2 with 1N HCl. The crude acid was extracted three times with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated.

Workup

  1. extractionThe crude acid was extracted three times with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9dc638f077a34471a6aae4b7ce251c69
Source dataset
uspto-grants-2013_01
Patent number
US08354545B2

Reaction notes

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