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804088 Sigma-Aldrich

SnAP 2-Spiro-(4-Pip) M Reagent

Synonym: tert-butyl 4-(aminomethyl)-4-((tributylstannyl)methoxy)piperidine-1-carboxylate

  • Empirical Formula (Hill Notation) C24H50N2O3Sn

  • Molecular Weight 533.38

  •  PubChem Substance ID 329768843

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Properties

Related Categories Chemical Synthesis, Organometallic Reagents, SnAP Reagents More...
InChI Key   LEBKPKYDLQUOJO-UHFFFAOYSA-N
form   liquid
refractive index   n/D 1.492
density   1.146
storage temp.   −20°C

Description

General description

SnAP (Sn amino protocol) reagents have been developed by the Bode group SnAP reagents are air and moisture stable. They can be prepared by simple reactions with cheap raw materials. SnAP 2-Spiro-(4-Pip) M, also referred to as SnAP 2-spiro-(4-piperdine) morpholine, is a regioisomeric SnAP reagent. This reagent can be prepared from N-Boc piperidone.

Application

SnAP Reagents provide a one-step route, in tandem with various aldehyde substrates, to saturated N-heterocycles. The synthesis of N-heterocycles through SnAP Reagents requires mild reaction conditions, and aldehydes bearing aryl, heteroaryl, glyoxyl, aliphatic, and halogenated groups are well tolerated. This product was introduced in collaboration with the Bode Research Group

SnAP 2-Spiro-(4-Pip) M Reagent may be used for the preparation of unprotected, saturated N-heterocyclic compounds, C-substituted bicyclic and spirocyclic morpholines.

Packaging

500 mg in glass bottle

Other Notes

Technology spotlight: SnAP Reagents
Professor product portal: Jeffrey Bode Research Group
SnAP Reagents for the Synthesis of Piperazines and Morpholines
SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes
SnAP Reagents for a Cross-Coupling Approach to the One-Step Synthesis of Saturated N-Heterocycles
Bespoke SnAP Reagents for the Synthesis of C-Substituted Spirocyclic and Bicyclic Saturated N-Heterocycles

Safety & Documentation

Safety Information

RIDADR 
UN 2788 6.1 / PGIII

Documents

Certificate of Analysis

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Protocols & Articles

Articles

Jeffrey Bode Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Jeffrey Bode Group – Professor Product Portal
Keywords: Annulations, Asymmetric synthesis, Catalysis, Cross couplings, transformation

SnAP Reagents

Saturated N-heterocyclic building blocks are of growing importance but their installation has been challenging due to poor commercial availability and the often long, laborious synthetic routes neede...
Keywords: Building blocks, Chromatography, Column chromatography, Purification

Peer-Reviewed Papers
15

References

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