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804088

Sigma-Aldrich

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

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C24H50N2O3Sn
Peso molecolare:
533.38
Codice UNSPSC:
12352103
ID PubChem:
NACRES:
NA.22

Stato

liquid

Indice di rifrazione

n/D 1.492

Densità

1.146

Gruppo funzionale

amine
ether

Temperatura di conservazione

−20°C

Stringa SMILE

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;
LEBKPKYDLQUOJO-UHFFFAOYSA-N

Descrizione generale

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.

Applicazioni

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.

Automate your N-heterocycle formation with Synple Automated Synthesis Platform (SYNPLE-SC002)

Prodotti correlati

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Descrizione
Determinazione del prezzo

Avvertenze

Danger

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

>230.0 °F

Punto d’infiammabilità (°C)

> 110 °C


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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

Protocolli

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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