tert-Butyl 3-(1H-imidazol-2-yl)azetidine-1-carboxylate → 2-(3-Azetidinyl)-1H-imidazole

HRID 1913148Notes

Reaction equation

HRID 1913148 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1>C(Cl)Cl>[NH:8]1[CH2:9][CH:6]([C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH2:7]1

Participants

3

Reactant 1

HCID 58494519tert-Butyl 3-(1H-imidazol-2-yl)azetidine-1-carboxylate

Product 1

HCID 552991962-(3-Azetidinyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(1H-imidazol-2-yl)azetidine-1-carboxylate (36 mg, 0.16 mmol) in DCM (1 mL) is added boron trifluoride diethyl ether complex (40 μL, 0.318 mmol). After 2 h the reaction mixture is quenched with water (11 μL). MeOH is added and the reaction mixture is concentrated under reduced pressure to give crude 2-(azetidin-3-yl)-1H-imidazole.

Workup

  1. customAfter 2 h the reaction mixture is quenched with water (11 μL)
  2. additionMeOH is added
  3. concentrationthe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-57913568981c4ce98146f925d343f321
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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