Trifluoroacetic acid → 4-(2-Cyclopropyl-2-phenyl-ethyl)-pyridin-2-ylamine

HRID 1023434Notes

Reaction equation

HRID 1023434 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][CH:15]([CH:22]2[CH2:24][CH2:23]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH:22]1([CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH2:7])[CH:13]=2)[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 69085979[4-(2-Cyclopropyl-2-phenyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 690836834-(2-Cyclopropyl-2-phenyl-ethyl)-pyridin-2-ylamineYield 102.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The crude [4-(2-cyclopropyl-2-phenyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (97 mg) is dissolved in DCM (1.5 mL) and trifluoroacetic acid (0.5 mL) is added. After the mixture is stirred for 16 hrs, EtOAc (25 mL) is added followed by the addition of saturated NaHCO3 aqueous solution (10 mL) and water (15 mL). The mixture is stirred for 15 min and the aqueous layer is separated and extracted with EtOAc (2×25 ml). All the organic layers are combined and concentrated to give 70 mg of the crude product which is used in the next step without purification.

Workup

  1. stirringThe mixture is stirred for 15 min
  2. customthe aqueous layer is separated
  3. extractionextracted with EtOAc (2×25 ml)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1171312f6aba41509414743c515eaa1a
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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