Trifluoroacetic acid → 3-(1-(4-Chlorophenoxy)ethyl)azetidine

HRID 522878Notes

Reaction equation

HRID 522878 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]([CH:9]2[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH3:8])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH:9]2[CH2:10][NH:11][CH2:12]2)[CH3:8])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86685242Tert-butyl 3-(1-(4-chlorophenoxy)ethyl)-azetidine-1-carboxylate

Product 1

HCID 673546353-(1-(4-Chlorophenoxy)ethyl)azetidineYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with tert-butyl 3-(1-(4-chlorophenoxy)ethyl)azetidine-1-carboxylate (140 mg, 0.449 mmol) was added CH2Cl2 (1796 μL) followed by TFA (242 μL, 3.14 mmol). The reaction mixture was stirred at RT for 72 h. The yellow solution was dried under reduced pressure and purified with a 2 g SCX-2 column loading and washing with MeOH, then washing with 2M NH3 in MeOH to afford 3-(1-(4-chlorophenoxy)ethyl)azetidine (57 mg, 0.269 mmol, 60.0% yield, about 10% impurity present) as a light pink oil.

Workup

  1. customThe yellow solution was dried under reduced pressure
  2. custompurified with a 2 g SCX-2 column loading
  3. washwashing with MeOH
  4. washwashing with 2M NH3 in MeOH

Sources & evidence

ORD record
ord-73f6ca2024eb4202a5dbc331b3cdd8b9
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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