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

HRID 876557Notes

Reaction equation

HRID 876557 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.FC(F)(F)C(O)=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 82 (750 mg, 2.71 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (4.0 mL) at room temperature. The resulting reaction mixture was stirred at room temperature for 6 h and then concentrated under reduced pressure. Saturated aqueous Na2CO3 was added to the resulting residue until the solution pH reached 9. The mixture was then extracted with ethyl acetate (3×25 mL). The combined organic layers were dried with Na2SO4 and concentrated under reduced pressure to afford 49 (440 mg, 92% yield).

Workup

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

Sources & evidence

ORD record
ord-9c7b4f4c77394b61af23fe015595cd3d
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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