Trifluoroacetic acid → N-[(4-Chlorophenyl)methyl]-N-(2-methylpropyl)pyrrolidin-3-amine

HRID 242668Notes

Reaction equation

HRID 242668 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667581663-[(4-Chloro-benzyl)-isobutyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 23136981N-[(4-Chlorophenyl)methyl]-N-(2-methylpropyl)pyrrolidin-3-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(4-chloro-benzyl)-isobutyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester in dichloromethane cooled at 0° C. was added trifluoroacetic acid (20%) and warmed to room temperature and stirred for 2 h. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and free based with 10% aqueous sodium bicarbonate. The combined organics were dried over sodium sulfate and concentrated. The product was used without any further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe product was used without any further purification

Sources & evidence

ORD record
ord-139221f934324598aa155d7eacbc7410
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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