(S)-tert-Butyl 3-((2,4-dichlorobenzyl)amino)pyrrolidine-1-carboxylate → (S)-N-(2,4-Dichlorobenzyl)pyrrolidin-3-amine

HRID 252086Notes

Reaction equation

HRID 252086 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH2:14][NH:13][C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 66854615(S)-tert-Butyl 3-((2,4-dichlorobenzyl)amino)pyrrolidine-1-carboxylate

Product 1

HCID 66569981(S)-N-(2,4-Dichlorobenzyl)pyrrolidin-3-amineYield 82.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Stir (S)-3-(2,4-dichlorobenzylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.08 g, 3.13 mmol) in 20% trifluoroacetic acid in dichloromethane (10 mL) overnight. Concentrate and dissolve the residue in methanol (2 mL) and deposit onto an SCX-cartridge; eluting with methanol, then with 2 N ammonia in methanol. Concentrate the ammonia washing to give the title compound (630 mg, 82%).

Workup

  1. concentrationConcentrate
  2. dissolutiondissolve the residue in methanol (2 mL)
  3. washeluting with methanol
  4. concentrationConcentrate the ammonia washing

Sources & evidence

ORD record
ord-b81238bdd3414aaa8a2ace07b21900eb
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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