Trifluoroacetic acid → 6-(Pyrrolidin-1-ylmethyl)pyridin-2-amine

HRID 85152Notes

Reaction equation

HRID 85152 reaction equation
[N:1]1([CH2:6][C:7]2[N:12]=[C:11]([NH:13]C(=O)OC(C)(C)C)[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>ClCCl>[N:1]1([CH2:6][C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66694553Tert-butyl 6-(pyrrolidin-1-ylmethyl)pyridin-2-ylcarbamate

Product 1

HCID 581545856-(Pyrrolidin-1-ylmethyl)pyridin-2-amineYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-(pyrrolidin-1-ylmethyl)pyridin-2-ylcarbamate (96; 750 mg, 2.7 mmol) in dichloromethane (10 mL) was added TFA (4.0 mL) at room temperature. The resulting reaction mixture was stirred at room temperature for 6 h and then concentrated under reduced pressure. Enough saturated aqueous Na2CO3 was added to the resulting residue to adjust the pH=9. The mixture was then extracted with ethyl acetate (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford 6-(pyrrolidin-1-ylmethyl)pyridin-2-amine 97 (440 mg, 92%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. additionEnough saturated aqueous Na2CO3 was added to the resulting residue
  4. extractionThe mixture was then extracted with ethyl acetate (3×25 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbbdec55aebe433ab00de1a622ab1f10
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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