Trifluoroacetic acid → Cyclobutanamine,1-(2-pyridinyl)-

HRID 1040489Notes

Reaction equation

HRID 1040489 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:8]1([NH2:7])[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58430865HCID 58430865, compound

Product 1

HCID 58431055Cyclobutanamine,1-(2-pyridinyl)-Yield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude (1-pyridin-2-yl-cyclobutyl)-carbamic acid tert-butyl ester (7.0 g, 5.64 mmol) was dissolved in DCM (20 mL) and TFA (20 mL) was added dropwise. After 6 h, the reaction was concentrated in vacuo and partitioned between DCM (100 mL) and water (20 mL). The aqueous layer was extracted with DCM (2×50 mL). The aqueous layer was then concentrated in vacuo. The brown oil was dissolved in water (3 mL) and purified via Mass-directed reverse phase HPLC purification which yielded 322 mg of 1-pyridin-2-yl-cyclobutylamine as a formic acid salt (yellow solid), m/z=149.5 [M+1]+.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. custompartitioned between DCM (100 mL) and water (20 mL)
  3. extractionThe aqueous layer was extracted with DCM (2×50 mL)
  4. concentrationThe aqueous layer was then concentrated in vacuo
  5. dissolutionThe brown oil was dissolved in water (3 mL)
  6. custompurified via Mass-directed reverse phase HPLC purification which

Sources & evidence

ORD record
ord-116e8cfe0dc740de85e84d76aaaf675d
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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