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tert-Butyl 3-(2-methoxy-2-oxoethylidene)azetidine-1-carboxylate

  • CAS No. 1105662-87-0

  • Cat. No. CS-M1516
  • Purity≥96%
  • MDL No.MFCD13190429

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

tert-Butyl 3-(2-methoxy-2-oxoethylidene)azetidine-1-carboxylate|CS-M1516

Structure of 1105662-87-0

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General Information

  • CAS No. 1105662-87-0
  • Cat. No. CS-M1516
  • Purity ≥96%
  • MDL No. MFCD13190429
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇NO₄
  • Molecular Weight 227.26
  • Synonym(s) 1-Boc-3-methoxycarbonylmethyleneazetidine
  • SMILES O=C(OC)/C=C1CN(C(OC(C)(C)C)=O)C\1

Description

tert-Butyl 3-(2-methoxy-2-oxoethylidene)azetidine-1-carboxylate features a strained azetidine core stabilized by a methoxy-substituted enol ether motif, enabling selective conjugate additions in complex molecule synthesis. The tert-butyl carbamate group offers excellent stability and convenient deprotection under mild acidic conditions. This reagent integrates readily into diverse synthetic sequences requiring nitrogen-containing heterocycles with defined stereochemical control.

Application

tert-Butyl 3-(2-methoxy-2-oxoethylidene)azetidine-1-carboxylate serves as a stable, bench-ready azetidine building block featuring a reactive α,β-unsaturated carbonyl moiety. It enables efficient Michael additions and cycloadditions, facilitating rapid access to functionalized azetidine scaffolds. The tert-butyl ester group provides excellent stability and ease of purification, while the methoxy-substituted enone system offers tunable reactivity for downstream transformations in medicinal chemistry and process development.

Synthesis

  • Route1

    References

    • WO2009/10488 A1, ; Page/Page column 47 ; WO 2009/010488 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   55.84
  • LogP   1.3365
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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