Trifluoroacetic acid → 4-(Azetidin-3-yloxy)pyridine

HRID 2171683Notes

Reaction equation

HRID 2171683 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][CH:8]2[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>ClCCCl>[NH:10]1[CH2:11][CH:8]([O:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24902675Tert-butyl 3-(pyridin-4-yloxy)azetidine-1-carboxylate

Product 1

HCID 509882824-(Azetidin-3-yloxy)pyridineYield 90.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

tert-Butyl 3-(pyridin-4-yloxy)azetidine-1-carboxylate (494 mg) was mixed with DCE (5 ml), and TFA (2 ml) was added thereto, followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (CHCl3/MeOH) to obtain 4-(azetidin-3-yloxy)pyridine (268 mg).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified by basic silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-df85a70c7d7544fe8f6d05a1f75d664d
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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