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CS-W001157 4
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tert-Butyl 3-oxoazetidine-1-carboxylate

  • CAS No. 398489-26-4

  • Cat. No. CS-D0675
  • Purity≥97%
  • MDL No.MFCD01861741

*For research and further manufacturing use only, not for direct human use.

tert-Butyl 3-oxoazetidine-1-carboxylate|CS-D0675

Structure of 398489-26-4

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General Information

  • CAS No. 398489-26-4
  • Cat. No. CS-D0675
  • Purity ≥97%
  • MDL No. MFCD01861741
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₃NO₃
  • Molecular Weight 171.19
  • Synonym(s) N-Boc-3-azetidinone
  • SMILES O=C(OC(C)(C)C)N1CC(C1)=O

Description

tert-Butyl 3-oxoazetidine-1-carboxylate features a strained azetidine ring with a carbonyl at the 3-position, enabling direct functionalization at the C3 carbon. The tert-butyl ester group provides stability and ease of removal under mild acidic conditions. This scaffold serves as a key building block for synthesizing bioactive molecules in medicinal chemistry.

Application

tert-Butyl 3-oxoazetidine-1-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling the construction of azetidine-containing scaffolds prevalent in medicinal chemistry. The ketone functionality facilitates nucleophilic addition and enolate formation, while the tert-butyl ester group offers stability and ease of removal under mild acidic conditions. Its reactivity profile supports diverse transformations including reductive amination, conjugate addition, and ring expansion, making it a practical intermediate for the synthesis of bioactive heterocycles and API candidates.

Synthesis

  • Route1

    References

    • Journal of the American Chemical Society, , vol. 135, # 42 p. 15742 - 15745
  • Route2

    References

    • EP2287173 A1, ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3335
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   46.61
  • LogP   0.8062
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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