Trifluoroacetic acid → (4-Chloro-benzyl)-isopropyl-pyrrolidin-3-yl-amine

HRID 242671Notes

Reaction equation

HRID 242671 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH:14]([CH3:16])[CH3:15])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:13]([CH:14]([CH3:15])[CH3:16])[CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667575503-[(4-Chloro-benzyl)-isopropyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 23137053(4-Chloro-benzyl)-isopropyl-pyrrolidin-3-yl-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[(4-chloro-benzyl)-isopropyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester in dichloromethane cooled at 0° C. was treated with trifluoroacetic acid (20%) and warmed to room temperature and stirred for 2 hours. 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. The product was used without any further purification. ESI-MS m/z: 253 (M+1, UV retention time: 0.59 min.

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. customThe product was used without any further purification

Sources & evidence

ORD record
ord-088bf83b9a9f479091611eb5f6645c4a
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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