Water → Benzoic acid, 4-(1-pyrrolidinylcarbonyl)-

HRID 1093799Notes

Reaction equation

HRID 1093799 reaction equation
O[Li].O.C[O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])=[CH:9][CH:8]=1.C1COCC1.O>CO>[N:15]1([C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:20])=[O:5])=[CH:8][CH:9]=2)=[O:14])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 17178210Methyl 4-(pyrrolidine-1-carbonyl)benzoate

Product 1

HCID 10932939Benzoic acid, 4-(1-pyrrolidinylcarbonyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

DIPEA (1.26 g, 9.7 mmol) was added to a stirred solution of terephthalic acid monomethyl ester (500 mg, 2.77 mmol) in DMF (3 mL) followed by HOBt (410 mg, 3.0 mmol) and EDCI (1.32 g, 7.0 mmol). After 2 minutes of stirring, pyrrolidine (215 mg, 3.0 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with cold water, the precipitate was collected to afford 53 mg (81.9% Yield) of 4-(pyrrolidine-1-carbonyl)-benzoic acid methyl ester. LiOH.H2O (285 mg, 6.8 mmol) was added to a solution of 4-(pyrrolidine-1-carbonyl)-benzoic acid methyl ester (530 mg, 2.27 mmol) in a mixture of methanol (2 mL), THF (6 mL) and H2O (2 mL). The reaction mixture was stirred at ambient temperature for 3 hrs. The reaction mixture was concentrated, the residue was diluted with water, and acidified with conc. HCl. The solid was filtered and dried to afford 41 mg (82.32% Yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. filtrationThe solid was filtered
  4. customdried
  5. customto afford 41 mg (82.32% Yield)

Sources & evidence

ORD record
ord-5fe70cd7498c4e808d818748bd499c6c
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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