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804088

Sigma-Aldrich

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C24H50N2O3Sn
Molecular Weight:
533.38
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

form

liquid

refractive index

n/D 1.492

density

1.146

functional group

amine
ether

storage temp.

−20°C

SMILES string

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;

InChI key

LEBKPKYDLQUOJO-UHFFFAOYSA-N

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.

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Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

804088-500MG:4548174010723
804088-BULK:
804088-VAR:


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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

Protocols

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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