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804088

Sigma-Aldrich

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C24H50N2O3Sn
Poids moléculaire :
533.38
Code UNSPSC :
12352103
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Forme

liquid

Indice de réfraction

n/D 1.492

Densité

1.146

Groupe fonctionnel

amine
ether

Température de stockage

−20°C

Chaîne SMILES 

CCCC[Sn](CCCC)(COC1(CCN(C(OC(C)(C)C)=O)CC1)CN)CCCC

InChI

1S/C12H23N2O3.3C4H9.Sn/c1-11(2,3)17-10(15)14-7-5-12(9-13,16-4)6-8-14;3*1-3-4-2;/h4-9,13H2,1-3H3;3*1,3-4H2,2H3;

Clé InChI

LEBKPKYDLQUOJO-UHFFFAOYSA-N

Description générale

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.

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Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Skull and crossbonesHealth hazardEnvironment

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 1

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

>230.0 °F

Point d'éclair (°C)

> 110 °C


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Consulter la Bibliothèque de documents

Kimberly Geoghegan et al.
Organic letters, 17(8), 1934-1937 (2015-03-31)
The precise placement of C-substituents on bicyclic and spirocyclic N-heterocycles is readily achieved by the combination of aldehydes and new SnAP reagents. The substituted SnAP reagents are readily prepared from simple starting materials and couple with a variety of aromatic
SnAP Reagents for a Cross-Coupling Approach to the One-Step Synthesis of Saturated N-Heterocycles.
Luescher MU, et al.
Aldrichimica Acta, 48(2), 43-48 (2015)
Cam-Van T Vo et al.
Nature chemistry, 6(4), 310-314 (2014-03-22)
Interest in saturated N-heterocycles as scaffolds for the synthesis of bioactive molecules is increasing. Reliable and predictable synthetic methods for the preparation of these compounds, especially medium-sized rings, are limited. We describe the development of SnAP (Sn amino protocol) reagents

Protocoles

Saturated N-heterocyclic building blocks or SnAP Reagents are of growing importance for the convenient synthesis of medium-ring saturated N-heterocycles, including bicyclic and spirocyclic structures. SnAP reagents are stable and readily available and can be coupled with widely available aromatic, heteroaromatic, aliphatic, and glyoxylic aldehydes.

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