Trifluoroacetic acid → 1-(5-Trifluoromethylpyridin-2-yl)azetidin-3-ylamine

HRID 2109514Notes

Reaction equation

HRID 2109514 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:11][N:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][N:13]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:21][C:18]([F:19])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([N:10]2[CH2:9][CH:8]([NH2:7])[CH2:11]2)=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69055899[1-(5-Trifluoromethylpyridin-2-yl)azetidin-3-yl]carbamic acid t-butyl ester

Product 1

HCID 100820621-(5-Trifluoromethylpyridin-2-yl)azetidin-3-ylamineYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

D6 (750 mg, 1.28 mM) in dichloromethane (5 ml) was treated with trifluoroacetic acid (5 ml) overnight at ambient temperature. The solution was concentrated and then partitioned between dichloromethane and 2M sodium hydroxide. The dichloromethane solution was washed with brine, dried and concentrated to give the title compound as a colourless solid, (477 mg).

Workup

  1. concentrationThe solution was concentrated
  2. custompartitioned between dichloromethane and 2M sodium hydroxide
  3. washThe dichloromethane solution was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8e1d532e6c224ff0bccba3248ad38f9a
Source dataset
uspto-grants-2009_04
Patent number
US07514562B2

Reaction notes

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