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

Name: SnAP 2-Spiro-(4-Pip) M Reagent
Brand: ALDRICH

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:

329768843

NACRES:

NA.22

form

liquid

refractive index

n/D 1.492

density

1.146

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.

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

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

related product

Product No.

Description

Pricing

signalword

Danger

hcodes

H301,H312,H315,H319,H360FD,H372,H410

pcodes

P202 - P273 - P280 - P301 + P310 - P302 + P352 + P312 - P305 + P351 + P338

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

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

wgk_germany

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

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Bespoke SnAP reagents for the synthesis of C-substituted spirocyclic and bicyclic saturated N-heterocycles.

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)

SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes.

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

SnAP Reagents

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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