Potassium Carbonate → 3-(3-Pyridyl)-1-propyl pyrrolidine-2-carboxylate

HRID 1937452Notes

Reaction equation

HRID 1937452 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:14])=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.FC(F)(F)C(O)=O>[NH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:14]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 154276653-(3-Pyridyl)-1-propyl (2s)-n-(tert-butyloxycarbonyl)-pyrrolidine-2-carboxylate

Product 1

HCID 154276663-(3-Pyridyl)-1-propyl pyrrolidine-2-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(3-pyridyl)-1-propyl (2S)-N-(tert-butyloxycarbonyl)pyrrolidine-2-carboxylate (3.00 g; 9 mmol) in methylene chloride (50 mL) and trifluoroacetic acid (5 mL) was stirred at room temperature for three hours. Saturated potassium carbonate was added until the pH was basic, and the reaction mixture was extracted with methylene chloride (3×). The combined organic extracts were dried and concentrated to yield 2.00 g (95%) of the free amine as a thick oil. 1H NMR (300 MHz, CDCl3): δ 1.87-2.20 (m, 6H); 2.79 (m, 2H); 3.03 (m, 2H total); 3.07 (m, 2H); 3.84 (m, 1H); 4.24 (m, 2H); 7.32 (m, 1H); 7.60 (m, 1H); 8.57 (m, 2H).

Workup

  1. extractionthe reaction mixture was extracted with methylene chloride (3×)
  2. customThe combined organic extracts were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dc4e0f8d3f3947a5b4d407bef9a43e6a
Source dataset
uspto-grants-2002_05
Patent number
US06395758B1

Reaction notes

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