Azetidine hydrochloride → HCID 58054144, compound

HRID 75119Notes

Reaction equation

HRID 75119 reaction equation
[C:1]([C@H:5]1[C:9](=[O:10])OC(=O)[NH:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH:13]1[CH2:16][CH2:15][CH2:14]1>C(O)C>[NH2:6][C@@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:9]([N:13]1[CH2:16][CH2:15][CH2:14]1)=[O:10]

Participants

4

Reactant 2

HCID 12308726Azetidine hydrochlorideHCID 5735175362965-56-4

Product 1

HCID 58054144HCID 58054144, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-4-tert-butyloxazolidine-2,5-dione (1.59 g, 10.12 mmol) and azetidine hydrochloride (0.946 g, 10.12 mmol) were combined in ethanol (5 mL) in a 2 mL microwave vial. The vial was capped and subjected to microwave irradiation at 150° C. for 10 min. The reaction was concentrated under reduced pressure and azeotroped with twice with toluene (5 mL) to provide the desired (S)-2-amino-1-(azetidin-1-yl)-3,3-dimethylbutan-1-one as a brown oil (1.7 g, 99%) that was used without further purification. LCMS (+ESI) m/z: 171.1 [M+H]+.

Workup

  1. customThe vial was capped
  2. customirradiation at 150° C. for 10 min
  3. concentrationThe reaction was concentrated under reduced pressure
  4. customazeotroped with twice with toluene (5 mL)

Sources & evidence

ORD record
ord-e3a384bcc62c4070b1025ff8155f2fa6
Source dataset
uspto-grants-2014_09
Patent number
US08835422B2

Reaction notes

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