1(2H)-Quinolinecarboxylic acid, ethyl ester → N-Boc-pyrrolidine

HRID 71817

Reaction equation

HRID 71817 reaction equation
NC1C=CC(C(NC2C=CC(N)=CC=2)=O)=CC=1.[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1C(O)=O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(OC(N1C2C(=CC=CC=2)C=CC1)=O)C>C(Cl)Cl>[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 278131(2H)-Quinolinecarboxylic acid, ethyl esterHCID 699174,4'-DiaminobenzanilideHCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 643455N-Boc-pyrrolidineYield 146.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-N-(4-amino-phenyl)-benzamide (3.00 g) and pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (6.55 g) were dissolved in DCM (90 mL), and 1-ethoxycarbonyl-1,2-dihydroquinoline (7.88 g) was added. The reaction mixture was stirred at ambient temperature for 17 hours and evaporated under vacuum. Oil was dissolved in ethyl acetate, forming a precipitate, which was collected by vacuum filtration and dried under vacuum, giving 2-(4-{-4-[(pyrrolidine-1′-carboxylic acid tert-butyl ester)-phenylcarbamoyl}-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (7.64 g, 93%) as a white solid.

Workup

  1. customevaporated under vacuum
  2. dissolutionOil was dissolved in ethyl acetate
  3. customforming a precipitate, which
  4. filtrationwas collected by vacuum filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-851abe264ae2447caeeeb1878922558d
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Linked notes

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