Trifluoroacetic acid → (2-Chloro-benzyl)-((rac)-2-methyl-pyrrolidin-2-ylmethyl)-amine

HRID 1644802Notes

Reaction equation

HRID 1644802 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:19][CH2:18][CH2:17][C:16]1([CH2:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[CH3:20])=O)(C)(C)C>C(Cl)Cl>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][NH:22][CH2:21][C:16]1([CH3:20])[CH2:17][CH2:18][CH2:19][NH:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66774296HCID 66774296, compound

Product 1

HCID 66773093(2-Chloro-benzyl)-((rac)-2-methyl-pyrrolidin-2-ylmethyl)-amineYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (4 mL) was added to the solution of (rac)-2-[(2-chloro-benzylamino)-methyl]-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.4 g) in DCM (15 mL) at 0° C. and stirred the reaction mixture at rt for 12 h. The reaction was monitored by TLC. After completion, the reaction mixture was concentrated under reduced pressure using a rotary evaporator and washed with ether (3×10 mL). The crude was basified with sodium bicarbonate and the aqueous layer was extracted with DCM (3×50 mL). The organic layer was dried over anhydrous Na2SO4 and distilled using rotary evaporator to give the desired (2-chloro-benzyl)-((rac)-2-methyl-pyrrolidin-2-ylmethyl)-amine as a sticky solid (Yield 40-70%).

Workup

  1. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure
  2. customa rotary evaporator
  3. washwashed with ether (3×10 mL)
  4. extractionthe aqueous layer was extracted with DCM (3×50 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. distillationdistilled
  7. customevaporator

Sources & evidence

ORD record
ord-9579b7d165e043978f69672d61696443
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Reaction notes

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