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

HRID 635246Notes

Reaction equation

HRID 635246 reaction equation
C(OC([N: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])=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 538856423-(3-Pyridyl)-1-propyl N-(tert-butyloxycarbonyl)pyrrolidine-2-carboxylate

Product 1

HCID 154276663-(3-Pyridyl)-1-propyl pyrrolidine-2-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(3-pyridyl)-1-propyl N-(tert-butyloxycarbonyl)pyrrolidine-2-carboxylate (3.0 g; 8.9 mmol) in methylene chloride (40 mL) and trifluoroacetic acid (8 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 (3x). The combined organic extracts were dried and concentrated to yield 1.60 g (77%) of the free amine as a thick oil. 1H NMR (300 MHz, CDCl3): δ1.71-2.09 (m, 6H); 2.63 (m, 2H); 2.86 (m, 1H); 2.94 (m, 1H); 3.71 (m, 1H); 4.11 (m, 2H); 7.18 (m, 1H); 7.45 (m, 1H); 8.41 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-02617a4256194512a4eb017a91190b30
Source dataset
uspto-grants-2001_02
Patent number
US06187796B1

Reaction notes

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